Money Sex
Author: Hannah Jay
Date: 2016-11-04 04:00:00+00:00
Publisher: UNKNOWN

Contents

Introduction

Jane

Artful Escorting

Annie | Tonya | Kelly

Back to School – College Escorting 101

Rachel

Escorting the Hedgies

Juliana

The Luxury Approach

Trish

Mile High Escort

Sybil

Lesbian Experience

Elise

A month at a time

Martine

Playing the Part

Jasmine | Bree | Candace | Rosy

Escort Style

Charlie

Private Dancer: A stripper and an escort

Introduction

In the course of writing Avails: Escorting for the Elegant Woman, Questions for Miss Jay: An Escort's Guide to Style, Dates and Fun and Modern Mistress: Lead the Luxury Life You Deserve I had the good fortune to speak with literally hundreds of women who, for all sorts of reasons, decided to make the link between sex and money.

Each of these wonderful women approached the money/sex nexus from her own perspective and met her own needs. Some were “kept” in the old fashioned sense of being one man’s exclusive mistress, others escorted very occasionally, still others made a business of pleasure: all of the women I spoke to did, however, share one thing in common, they made their decision themselves.

When I interviewed escorts and mistresses I kept notes of our conversations. Some of the girls were very coy about “consenting adult activities”, others were deliciously graphic about the services they provided. Because I was focused on the higher end of the market, the women I spoke to tended to be articulate, smart and very savvy. Most were college graduates and many used escorting as a way of financing businesses or art making or lives of interest and value.

I fear I have no interest at all in the lower reaches of the business. There is nothing glamourous or erotic about a five minute car date or twenty minutes in the dirty sheets of a “no tell motel”. I am interested in the glamour, the illusions and the erotics of an often beautiful young woman selling her favours and herself to a well off gentleman (or lady) caller.

This is the first of a series of books about the carriage trade of the escorting world. These girls enjoy the so called finer things in life, they stay in shape, they read, cook, dress beautifully and, so far as I can see, are, from all appearances, ladies.

For their privacy I have used their working names throughout. I have also changed any identifying details – cities, locations within cities, store names – to ensure my reader hears their stories rather than gains clues to their identity.

It is actually rather sad that these delightful women have to be protected in this way. Escorting, courtesanship, mistresshood are surrounded by a thicket of prohibitions, legal and social, which deny these women the right to choose their profession. In fact, these women are bringing gifts to the men who patronize them. They are leading good lives, building real businesses and bringing a bit of joy into what are often rather dreary worlds. Rather than being scorned, insulted and even arrested, I believe these women should be celebrated for their courage and vitality.

This book is my celebration.

Jane

Artful Escorting

Do you have an image of an escort? Twenty something, tawny hair, sleek but with mildly oversized breasts and slightly too loud make up? Or brunette and sultry with pouty lips and an attitude? Or a Vegas showgirl with impossibly long legs gone bad. Or Catherine Deneuve in Belle de Jour looking all blond and French and bewildered?

All these images are right and all are equally wrong. There is no “typical” escort. In fact there is not even a typical escorting business. Some girls are purely service providers catering to hobbyists and hoping for great reviews, others are courtesans with a wealthy clientele who barely advertise much less solicit reviews. It is all about style and presentation and where a girl feels most comfortable. At the same time, an escort is in business and wherever she places herself on the escorting continuum has to create income.

We looked for a few girls who were both committed to escorting but willing to create businesses which suited their distinct needs and styles. We have talked to half a dozen and each is a long way from typical. Here’s Jane.

Jane’s Way

“I live in San Francisco.” Jane told us over Skype. “Which is incredibly expensive if you want a halfway nice place. I make art for a living and I am becoming pretty successful. But I am just starting so “pretty successful” means I sell a piece once in a while and I get into group shows. Unlike a lot of the people I went to art school with I don’t, as the expression goes, come from money. Exactly the opposite in fact. I sometimes have to send my mum money.”

“OK, I can’t live with roommates – they get in the way of art making - and I have a pretty simple one bedroom apartment in a fairly decent neighbourhood. But it is so expensive. And the problem is that even if I got a job all that would happen is I would have less time to make art and still not enough money.”

“All of which I was telling to a friend of mine a few years ago and she, a bit sarcastically, said, “Well, you could escort.” We both laughed. Except I didn’t really. When I went back to my apartment and looked at the piece I was working on I realized that escorting might be a perfect solution. I went online and, wow, what a zoo! I was on a couple of pretty down market sites and I just could not imagine doing this sort of work or being that sort of girl. No offence, but some of those girls were plain scary.”

I’m not scary. I’m all of five foot three with short boy cut hair and a very petite figure. I am, as my mother used to tell me, gamine which I swear is French for “boyish”. I spend most of my days in overalls and a t-shirt and a baseball cap covered in paint and glue. And I like doing that. Sure, I had a couple of more girly outfits but nothing at all which really was what I thought I should wear if I wanted to be an escort.

But I am nothing if not resourceful. If I was going to do this I was going to do it my way and that started with an ad saying, “Pretty 20 something girl needs advice and purchasing power of an older man. Getting ready to escort but I don’t have a thing to wear. Can you help?” I put in a selfie of me in my painting clothes. I kept my face out of the shot.

I put the ad up late on a Thursday night and went out to a movie. I was out for maybe four hours and I got 150 separate email response. Yes, several pictures of remarkably unattractive penises; but most of the emails were very nice. I took the ad down and got to work answering emails. What a lot of work.

Eventually I found four men who I thought would be fun to see and fun to shop with. A bit of back and forth on email was incredibly useful. One of them asked how I was “screening”. A term I was unfamiliar with. Believe it or not he walked me through checking out potential clients.

When I had looked at the other girls I barely noticed their rates and that was a question I was getting asked a lot. How much for how long? And did I? Then there were a list of activities. Lots of different activities most of which I had never heard of. What I did know was that I wanted to stay safe so I required a condom no matter what. But those guys were not what I was looking for to start out. I really did want to go out shopping with someone.

Larry was my first ever escort date. In his fifties, he was a lawyer from a big downtown firm where a friend of mine worked reception which made checking him out easy.  What a nice man. He suggested we meet for coffee which we did.

“So are you sure you want to do this?” he asked.

I admitted I was not at all sure. “But I would love to have the free time and some money.”

He didn’t try and talk me out of escorting. Quite the opposite.

“Here’s the point. Escorting is just like any other service business. You have clients, you set a fee, you do the job. But, and it is a big but, you don’t have to accept every client and, if anything, being selective makes you seem more valuable. Your fees need to reflect two things: the quality of service and how you want to be seen in the market place. But your fees are also a signal to your potential clients.”

We talked about “activities” and Larry suggested I stick to the basics. “If you are looking for older, better off, clients you don’t want to suggest you’ll do practically anything. When they see an escort the sex is part of the experience; but it is a long way from the whole thing and, even with Viagra, acrobatics are not necessarily a turn on. If you do the basics with lots of enthusiasm most men will be thrilled.”

I actually asked him what he thought I should charge. “Well, I bill out at $900 an hour. I don’t see all of that of course, but that gives you a bit of an idea.”

“So, what, $500?” I asked.

“Try $750. It’s not the top of the league in San Francisco, but set a two hour minimum and you’ll do fine.”

Which is, more or less, what I did. Then we went shopping.

I was used to watching every penny. I have the feeling Larry hadn’t worried about less than a thousand dollars in years. But the funniest thing was that when we walked into the downtown Nordstrom – his pick – we were met by a personal shopper he arranged. Now I was wearing one of my “not an artist outfits” and this girl liked it. Nothing complicated, just a long grey cotton skirt, leggings and a white shirt on top of a tank top.

Larry was very smooth. I could see how he earned his money. “Jane would like to look a little less like an art student and a little more like a personal assistant to a venture capitalist. Day and evening, say three outfits for each. I’ll be back in an hour. And shoes, don’t forget shoes. And make sure you buy a couple of good garter belts Jane, I detest pantyhose.”

My personal shopper, who was named Amy, was very professional but she could not help but smile at the garter belts. Which Larry knew she would. “Dad” does not buy lingerie. We were off. Lots of lingerie, a pair of smart low heeled day shoes, a set of “once around the bed” Louboutins, and a pair of quite practical three inch heels.

“Do you want to stick with the boho thing or would you like to dress it up a bit?” asked my personal shopper. “What? How about boho by day, dressy past five?”

“Absolutely. You have nice legs so let’s do a couple of above the knee skirts for day time. Dresses for evening. A jacket or two. Is this one off or will you be shopping again?”

“I don’t know.” I said not knowing what Larry’s plans were.

“Looking at you and how “good” clothes fit you I suspect you’re going to be here quite often. So we won’t go over the top. And three of these items and two pairs of the shoes are on sale. Now, we just have time for Jean down on the Charlotte Tilbury counter for a little makeup and your delightful gentleman will not recognize you.” Off we went and ten minutes later I had a bag of cosmetics, an eyelash curler and cheekbones I never knew existed. “Now, a black tote bag and we’re done.”

“I wish we had time to have your hair cut but here is Harry’s card. Brilliant. And here is mine.” she said as we walked down the main aisle on the fashion floor. There was Larry standing surrounded by beautifully boxed and wrapped clothing, shoes, lingerie, stockings and I honestly don’t know what else.

“You look beautiful.” was all he said and, followed by three rather envious salesgirls we went out the door to an Uber SUV.  Smart. The sales girls loaded up the back and we climbed in. Because, Uber, Larry didn’t have to tell the driver where to go.

“Now, I want to see everything you bought and the best way to do that is to enjoy a suite before dinner if that is alright with you. As it happens our firm’s suite is empty tonight so…”

And off we went. Just up the hill, which describes almost anywhere in San Francisco. Larry had an overnight bag and I had half of Nordstrom. My clever personal shopper had even put a pretty, if tiny, silk nightie/chemise in amidst the lingerie. We were whisked – which is how it is always put – to the lovely one bedroom suite.

It was the most natural thing in the world to model my new clothes. One outfit at a time starting with day wear with, of course, flashes of the carefully chosen lingerie, and moving to a scintillating little black dress which was ideal for cocktails which we proceeded to have in the suite.

“Room Service, or should I show you off?” asked Larry. “I think I’ll show you off. Don’t bother to change.” he said laughing. We went to the elevators and, to my surprise, went up, rather than down. Yes, rooftop dining with the city at our feet. I had the feeling Larry had done this before so I asked.

“Well, yes. But this is my first time with a girl who is doing this for the first time. But I think if you are going to escort you might as well start at the top. You are certainly pretty enough. And I thoroughly enjoyed being teased this afternoon. You are a flirt under that artist tomboy exterior.”

So that is where I started. Larry took a little Viagra with his brandy and, a short elevator ride away, I slipped out of my little black dress and into my chemise. All went as expected. I was delighted to see a pleasingly average cock when it was time to go to work. I actually enjoy blow jobs when the cock in question is not too long and not too thick. Larry’s was just right. I did his first blow job in my chemise, long nude stockings, garter belt and panties. Which Larry seemed to very much enjoy.

Practice has taught me that a huge part of a great blow job is eye contact. As you are flicking his little head with your tongue, for Heaven’s sake look the lucky man straight in the eye before averting your gaze and taking him all the way in your mouth.

I’d decided that with an up market clientele, a bare back blow job was a minor risk. But I was not going to swallow. So when Larry was ready to shoot I knelt in front of him and said, “Cover me in your sweet cum Larry.” Words are very powerful and, in two strokes, he was happily squirting a pearl necklace over my face and upper chest. I directed the goo and, having taken the shoulder straps of my chemise off a bit earlier I was able to pull down my top to catch the last delicious drops on my pretty tits.

And then I remembered something an old boyfriend had liked. After licking the last of his mess off the end of his cock, I began rubbing his cum into my skin wherever it had squirted. I took my time and my eyes never left his as I spread his sticky cum over my cheeks, over my forehead, down my neck and into my already hard nipples. I saw his cock twitching for the second round and said, “Not quite yet Larry…I want to have a nice, warm shower and be ready for you.”

Which is exactly what I did. All that cum was rinsed off and I scented myself carefully. Before rejoining Larry I lubed my pussy. Not too much, I was already very wet, but a man likes to think he has his little whore really excited and the lube adds to the sensation. I left off my chemise and panties but put my stockings, cinch waist garter belt and heels back on. And I put on a hotel supplied dressing gown. I didn’t bother to do it up. A couple of quick nipple pinches and I walked back into the suite.

“For a beginner you certainly show a lot of promise.” said Larry as I walked over to the bed. He was naked but under the sheet.

“Thank you kind sir, I like to try. But I see you are ready to try out the rest of my skills. Did you put your condom on?”

“Yes.”

“Wonderful. You know what I just love?” I asked getting onto the bed beside him as I stepped out of my dressing gown.

“No, what?”

I knelt on the bed and slipped a couple of the 500 thread count pillows under my hips.

“I love it when a man takes me from behind, just my pussy. My backdoor is another date. But just push in and fuck me. No reach around. Just my ass up and my head down until you are done.” I put my head on the bed and looked up at Larry.

He didn’t have to be asked twice and I soon felt his nice, average, cock pounding away at my wet, lubed pussy. He loved not having to pay any attention to my pleasure and, honestly, I loved that too because I had one more trick up my sleeve.

It didn’t take long for my dripping, clenching pussy to push Larry over his edge and he rolled off me entirely satisfied. I had spotted the tissues and made something of a production of slipping his surprisingly full condom off and licking his cock clean again. Thank heavens for Viagra because, before I was done I could see a little life in what would, under normal circumstances, have been a very limp dick.

I lay beside Larry, making sure that one of my breasts was resting on his chest and I lifted one of my stockinged legs up onto his thigh. I let him rest a bit whispering how much I loved his perfect cock taking me doggy style. I mentioned my backdoor tingling as he fucked me – and yes, a good girl always says “fuck” and “cunt” in bed – so he would have the possibility for next time. And then, as I spoke I reached down and began to play with my genuinely soaking cunt. Being fucked from behind is something I have always loved. But I never come that way. So, years ago, I realized I would have to bring myself off.

I think most girls masturbate but I had learned from that same old boyfriend to be very comfortable, excited in fact, to masturbate myself for the man who had just fucked me. Now, if I want to I can snap off an orgasm in a minute or two, or I can take my time. With Larry I took my time. He couldn’t see me when I began touching my little clit which was already nicely engorged from her earlier fucking. He felt my hand against my pussy and, he’s a smart guy. I ground a bit on his thigh. But doggy style really does not get the job done. Which is fine, I like the feeling of being taken. And for me sex is about those sorts of feelings as much as the actual physical contact.

As I stroked myself I got wetter and I could see Larry realize what I was doing. As soon as he did, to my delight, his lovely, cut, prick began to find strength it never had. I rolled on the second condom of the evening before I got too distracted with my own pleasure.

“Have you ever watched a girl masturbate Larry. Play with her cunt for you?” I asked as I was beginning to get close. I rolled over on my back and Larry looked as if he was thinking of mounting me. “No, you just lie there and get hard and watch me make myself all wet for you.”

Even taking my time I was very close, pulsing, nipples throbbing, in all of three minutes. It was time.

Not saying a word, and still wearing my stockings and heels, I rolled onto my knees astride Larry’s hips. I could feel his nice, average, cock at the spread lips of my pussy and I slide up and down his shaft, catching my clit on the roll of the condom. I had my hands on his chest. I was completely in charge.

I reached back with one hand and angled his cock up into my very nearly gushing cunt. I pushed back until he was all the way in and then lifted myself to accommodate my own hand.

“Put your hands under your bottom Larry and don’t you dare thrust unless I tell you too.” I said knowing the combination of his cock up my cunt and my own fingers on my hard little clit would push me over in just a few, slow, strokes. I pinched his right nipple between my long, blunt, artist’s nails and began to feel him grow absolutely hard. I loved that sensation. My tight little cunt completely engulfed him and, while I didn’t let him push, I could. In a moment or two I was at the edge and then, to my huge surprise, falling into the arms of a tremendous orgasm. I kept Larry still as I rode the waves and then, when I was completely done, I said, “Now, slowly, you may begin to push into me. I am going to pinch your nipples hard when I want you to come. Understand?”

“Yes.” he gasped thrusting into me. Once the last waves of my orgasm are complete I quite like the sensation of being filled with a gentle, tame, cock. But not for too long, a minute or maybe three and then it is time. I pinched his nipples. Both nipples and was rewarded with his final orgasm. Underneath me. Where he belonged.

Lovely.

Larry left late. “I’ve extended checkout for you so enjoy the suite. I’ve ordered a suitcase for you as well and you can use my Uber account.” He gave me a fatherly peck on the cheek and as he did left a thick ivory envelope on the night table.

I lay in that vast bed with the perfectly crisp, only slightly rumpled, sheets surrounding me and I wondered what the heck I was doing. But I knew. The question was would I do it again?

I woke up, got packed and realized that my first adventure in the escorting trade had gone unbelievably well. Full on “Pretty Woman” which just does not happen. Except it did. Now, would it happen again? Just as I was wondering there was a knock on the door and a bellhop arrived with coffee, croissants, flowers and a note. “I am away for two weeks but will be calling on my return. Thank you, L.”

So, sipping my coffee, I realized that I had two weeks and two thousand dollars and a suitcase full of gorgeous new clothes. Rent was paid. I didn’t have to see anyone else and Larry would be back. Which was all good, but a part of me wanted to see if I could escort and one date, no matter how perfect, is not quite it.

I decided to get in touch with the other men on my short list. It turned out that each of the other men I had screened from that first escorting ad were all interested. Each was older and each was more than willing to play the escorting game my way.

Larry had suggested that I concentrate on developing a very discerning clientele. Older, well off, a bit fatherly, interested in very safe encounters with a very low volume girl. “You’ll make more money and the risks are removed.”

He was right. Instead of coming to escorting from a place where I was desperate for money – which I had been – I came to it as someone who was worth the price she asked her clients to pay. That simple reversal meant that all of a sudden I had the power in my escort dates.

That power began with the fact I screened very hard. Not only did I have to be able to establish a potential client’s identity and contact information, I also decided that I wanted to spend a bit of time on the phone or over coffee before accepting a new client. Yes, this did slow things down at first. But it meant I never saw anyone I was even slightly uncomfortable with.

My two hour minimum rule worked very well and so did my policy of not watching the clock at all. I went over time a few times but what is half an hour to ensure that a gentleman will be coming back again and again.

I realized that if I wanted to have time to make art I needed to be very disciplined about my escorting. I set a basic target of three dates a week which provided me with all the money I needed. I soon learned that most of my clients preferred to see me mid-week. And I discovered that my clients, for one reason or another, liked to see me in one of four or five good hotels. Plus, and this was a bit of a surprise, I had as many mid to late afternoon dates as I did evening encounters. All of which was just fine with me.

I have kept my advertising minimal. Once a month I place a small, discreet ad looking for “discerning gentlemen” and promising “an afternoon or evening of pleasure, laughter and conversation with a sophisticated, gamine, muse”.  I have a small picture in black and white and my face remains in shadow. I don’t get quite the rush of business my first escort ad provoked but I usually find three or four gentlemen to add to my roster. Which is all I need really.

I am into my third year escorting. The business is running itself and I am usually booked a couple of weeks in advance. I could see more clients but I think it would get pretty difficult to deliver a really quality service if I saw more than a few a week. I have raised my rates however. Not for my existing clients, just for new clients and that keeps my income very healthy.

My way of escorting is not for everyone. I am lucky. I started very near the top. But I am also lucky because I escort to pay for my art and, because I can devote full time to my art, my work is getting better known and I am selling more.

Larry did indeed return and after our next encounter proposed an arrangement which we have to this day: he sees me twice a month at my normal rates but with a bit of shopping thrown in and no clock at all. I swear we keep my personal shopper, Amy, in designer clothes just on her commissions. Larry is wonderful and so generous. He likes to tease me about being his mistress but, as he has never proposed an allowance, I tease him right back about not being able to make a commitment. (I let him have my backdoor three times a year…It is not that I don’t like anal, I don’t really but Larry is very average; it is that a girl needs a treat to give a man who gives her so much. I pretend to be reluctant but very submissive and Larry loves it. You want to keep a man like Larry interested.)

My own plan is to keep escorting for at least the next two or three years. For me the whole transformation from starving artist to courtesan in the space of an hour is amazing. Being “Jane” takes me entirely away from art for a few hours which I think is actually good for my work. Plus, because “Jane” has a fair bit of cash from escorting I don’t get into the whole self-pity thing which I don’t think is good for artists. The cash plus “Jane’s” persona gives me a lot of self-confidence.

It funny how often I see Jane’s clients at my gallery openings and group shows. Once I have known a client for a while I will tell him my art name – which is also not my real name – and it is pleasing to see the little red dots land on my work. My clients are becoming my patrons which is very close to perfect.

Annie | Tonya | Kelly

Back to School – College Escorting 101

As summer winds down the great migration of college students all over North America is beginning. Bags are packed, computer stowed and, yikes, tuition fees paid. And in cities and towns all across America little ads begin to appear.

“College girl seeking company.” “A GFA with a college girl next door”; yes, many of the girls advertising have not been within a thousand yards of a campus in years. However, more than a few girls work as escorts to put themselves through college or just to have a bit of spending money.

Whether it is retail escorting, being kept as a mistress or occasionally going on a “paying date” college girls know that there is a real market for their companionship. How they approach this market while keeping up with their course work is an interesting balancing act. I spoke to three girls in three very different situations.

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Annie is a twenty five year old graduate student at a university on the Eastern seaboard. “I’m a little older than the typical college girl escort. I love university and I love doing advanced work in history. I suppose, eventually, I’ll get a “real job” but right now I like going to my seminars and writing my papers. What I didn’t like when I was an undergraduate was constantly being broke.

As an undergraduate the escorting thing was not really an option because I was in a really small college town a long way from the anonymity of the city. But I certainly looked at the possibility. So, when I was accepted into the graduate program I am in I very deliberately tested the escorting waters in the city the university was in.

Even before I moved to the city I was researching – PhD candidates are very good at researching – the business in that city. Based on my research I spotted what I thought would be a comfortable, up market, niche. The city is a fairly serious financial center and there are a lot of men travelling into town.

I was very deliberate. I wanted a certain sort of client. Older, well off, very safe. I read a lot about the business. Everything from advertising to protecting myself legally to how various girls organized their business. I didn’t need to make a fortune escorting. Just enough to cover a nice apartment and have a few treats. I had a fellowship which covered my tuition so it was just my living expenses I was worried about.

I wanted to keep my privacy. I had a nice apartment but in a small building and even a few different men arriving would have been suspicious. Obviously I didn’t want my fellow grad students or profs figuring out that I was escorting. Easy enough. I bought a dedicated smart phone which was switched off during the time I was on campus. I could check texts, emails and messages discretely but I usually did not return the calls until I had lunch, off campus, and again on my way home. Of course, one of the pleasures of graduate student life is that I only had classes two days a week. For extra privacy, I never went directly from campus to a date so my peers never saw my escort look.

I paid attention to that “look”. I wanted to have a polished, professional style even though I was planning on advertising as a student. Because I knew the gentlemen I was targeting would be older professionals and there was no way I could see them in the grad student uniform of jeans and a top or even a peasant dress. Again, I did my research and with a little money I had saved found a couple of smart pencil skirts and professional grade white cotton shirts. A couple of jackets and I looked like the sort of up and coming girl who drops off papers to business executives at odd hours of the evening. Now, underneath, and in my very demure advertising pictures, I was all about white, semi-sheer, lacy bras and pretty stockings: but on the outside I was all business. I had professional pictures done on a “Time for Prints”, in this case a CD, basis. Sexy, but a very long way from slutty. And my face never showed. Neither did anything more provocative that the outline of a nipple.

I wanted to see businessmen from out of town in good hotels. So that is exactly what I advertised for. “Attractive, intelligent, graduate student seeking evening conversations with discrete, older businessmen. Executive hotels only. Expensive but worth every penny. I never watch the clock. Dinner? Of course. Email preferred.” I put that ad up on a couple of the more exclusive escort advertising sites. And then I waited.

I didn’t have to wait long.

At my rates I needed two dates a week to do well, three to have plenty of treats. The day I put my ad up I had six emails, three realistic and booked two dates. The next day I had nine, five realistic and booked three more dates.

I was not the least bit nervous about my first “escort” date. I treated it like any other date. I met my client for a drink in the lobby of his hotel and, when we hit it off – which we did as he was a rather nice, if slightly balding, guy – we went up to his room. I always carry what is known as a lawyer’s bag on my dates. It is a really big leather brief case, about three times as thick as a regular brief case. In it I have everything from sexier heels to condoms to candles to unscented shower gel. A couple of toys, a riding crop and a little Bluetooth speaker for my smartphone. It is a great prop. What escort is going to carry that around? Well I do. And it serves me well.

Ninety percent of my dates are very “meat and potatoes” sex. I tease a little and then get down to sucking my client’s cock. Big, small, in between, men just love a girl who will, without asking, go down on them. Sometimes, if the guy seems nice, I will suck his cock without a condom. But, when I feel him getting ready to come, I always slide away. Who wants to swallow? (I will, but it is a very expensive extra.) But what I am usually doing is getting that cock ready for a condom and for my pussy.

I always make sure to lubricate before a date so when he’s ready, I’m ready. I am delighted to have a guy cum a couple of times during a date. With Viagra most of my dates are up at least twice and three or four times is not out of the question. But, past two, I insist on having my pussy licked. For a while. I never have a cock anywhere near my pussy without a condom. No regrets I say.

From that date forward I have been booked two or three evenings a week. As I say in my ad, I don’t watch the clock but on average, from drinks to taxi home is about two and a half hours. Dinner adds, at most an hour unless I am having a great time in which case, who cares.

On average I am making a little over $5000 a month. For a very part time commitment with no serious expenses I am pretty happy with that. I bank two thousand and keep the rest in cash for treats and fun. Almost all my dates are from Monday to Thursday. My clients like to fly out on Friday.

I’ve been doing this for two years and have a set of a dozen or so regulars who I see every month or, maybe, six weeks. Of course I prefer my regulars. Less hassle, no screening, usually a good dinner. My biggest problem is too many great meals. I have to make sure I work out on about a one to one ratio.

I don’t think escorting is for every girl. You have to be a little detached and really understand it’s a business. I see really young girls, 18 or 19, advertising and I am not sure they are ready. But, their choice. I’ve made mine and I’m happy with it.

Down the road? Well I have three years to finish my thesis. Then we’ll see. It is easy to escort when you are a student, not so easy if you have a real job. But I can’t see giving up my regulars. They are a really nice bunch of men.

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Tonya, twenty, vivacious on Skype and very, very blonde, has an entirely different story. She is at a Mid-Western school in a fairly big city.

I was in my second year as an undergraduate and I was just loving my courses and my profs. I like living on my own though. I lived in a dorm in first year and it was awful. I guess I am really private and I really, really like to study. The dorm was too loud, too much of a party. So I got a cute little apartment off campus with a room mate. Which worked great until my room mate decided to have a serious melt down and move out nine days before rent was due. I have a really nice landlord and I figured I’d tell him what the problem was and ask for an extension on the rent until I found a new room mate. He had another suggestion. Well, the rent was $500 and I have to admit I sort of like the idea of getting half off for a few consenting adult activities on the quiet a couple of times a month. So, I said yes.

I have to say he was a great way of getting into the business. Gentle, clean and not very demanding. In fact I would say he sort of lulled me into the whole thing. And once I had given my first “professional” blow job, the rest was pretty easy. My landlord is not the old fat smelly guy, he’s the ambitious, young, no time for a girlfriend guy.

The nice thing about my apartment is that it is very private. It is above a garage in a busy downtown neighbourhood. Lots of trees out back and a very simple layout: just a little kitchen, a nice big bathroom and a bedroom and living room all in one room divided by two of those Ikea cube shelving units. My door is up a flight of stairs and just off an alley one house in. I thought that it would be pretty easy to see clients without anyone really knowing what I was doing and I was right.

I needed a bit of money every month. My parents were financing my tuition and giving me a bit of extra money but it was really tight, even with half my rent being paid by my landlord. With the internet this was really easy. I put up an ad once in a while, had about a hundred calls every time.  I like the soccer dads. You know, the guys in the mini-vans with a couple of kid seats in the back. They are really safe, really grateful and some of them are kinda hot.

My ads are really basic. “College student available for GFE. Blonde, 34 D, love my work!” I am actually a C cup but I have never yet had a guy check. I don’t see many guys. I could, I guess, but I am really religious about screening. I want nice, clean, dads who have way more to lose than I do. And there they are parked at the end of my little alley.

I have to admit I really like dates around 7 in the evening. I’ll do one at 7, one at 8:30. No rush and I can go and hang with my girlfriends by 10 and they all think I’m a study bunny.

The sex? Blow jobs. I’d say 60% or more of the guys I see come five minutes into a blow job. It’s what they want. I am good at blow jobs. I can deep throat anything up to about eight inches which they love. But the secret is that a blow job is just a wet hand job with kisses. You swallow the sword a couple of time but mainly you are just jerking them off. They have to wear a condom so, no mess. My rates without a condom are double. So I suck cock most of the time and, once in a while, a guy will want to bang me which is fine but a bit boring. I mean I am there for them so I don’t get off very often.

A few guys will want to go down on me which, honestly, I wish they wouldn’t. It is sort of like kissing. I’ll kiss a date but I won’t like it. I like the soccer dads who just want a bit of unfamiliar flesh, a girl who wants to blow them. Totally worth it.

Biggest challenge? OK, this is weird, but way too much money. No, really. When I am not doing exams I can see two or three guys a night five days a week at $250-300 a guy. You do the math. 2000 to 3000 a week is what most of my girlfriends have to live on for a semester. It kinda shows. I try to be cool about it but girls notice a new bag or a really cute dress. I say my parents bought stuff or sent me money. But I really do have to be careful.

And, of course, there is the damned phone. I keep it turned off in school but if I turn it on and I have an ad running and I’m having coffee with a girlfriend nine calls in ten minutes begins to show. I don’t think they have a clue. But I am sure some of them think I run a giant drug empire or something.

The only other downside is that this is not that big a city. I see my clients all the time in the same places I like to go to. Most of them are really cool and there is no problem. But some of them feel they have to say Hi. Which is a little awkward if I am out with friends.

The way I am getting around that is that I keep my hair down on my dates and put it up the rest of the time. I mean I am still me but with my hair up I look just different enough that a client feels ok not recognizing me.

Long run? Look, I’m twenty, in second year. I don’t really even know what I want to major in. But, seriously, can you think of another business where a girl my age can make 10K a month working pretty part time? I can’t. I have two years of college left and I know I am going to escort through those. Beyond that? I want to travel. Maybe go to Australia where this is totally legal. I mean my main worry is that some cop will go on a crusade and catch me. Which would kill my parents. But I have never had a hassle yet. So, really, I don’t know. The cash is awesome.

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Two very different approaches and there are hundreds of other college girls each with their own take on escorting. Kelly, who is a twenty one year old art history student, has a radically different take on the escort business.

“I decided I wanted to have a lot of time to myself so I could really go deep with my studies. That takes money but money that I don’t have to put thirty hours a week into. I looked around and tried being a “sugar baby” for a while. Not my thing at all. I didn’t want to be someone’s pay to play girlfriend and a lot of the guys you meet are very unpleasant. But the idea itself was is not half bad.

When I came back for third year I had a bit of a plan. The big problem with sugaring is that the “boundaries” are badly defined. You get booty calls at 2 in the morning. On the other hand, very selective escorting when it works, has all the boundaries in place. The problem there is that it is hit and miss. Busy one week, dead the next. Plus, in the city I live in we have a very active “vice squad” and state law which is pretty hard on even higher end girls.

The solution I came up with was to start looking for several men who would enjoy pampering a pretty young college student in a mistress style relationship. Not sugar, not exactly escorting: rather an evening or an afternoon every couple of weeks for lunch or dinner and then a lovely, sensual, encounter. Which was pretty much what I put in my ad. Because it was not directly escorting I was able to put it in the companionship section of the advertising sites.

My dates were just that, dates. I always let the gentleman bring up the subject of money and I never set a price directly. Instead I would say that I very much appreciated generosity and I would always say that I liked to see my friends with no time limits and no more than twice a month. Some of my gentlemen pay me each time they see me, others prefer to make a monthly arrangement.

I entertain at home for the most part although I have seen men at their hotels. But the key thing is that I try to provide a wonderfully luxurious, genuinely non-rushed, encounter. If I see more than one man in a day it is because of an unavoidable scheduling problem. Right now I have a waiting list because I limit myself to six patrons at any one time. I know that restricts my income but seeing more would eat into my time and I don’t think I would provide the same, superior quality service.

I like older, very married, men. They are so very grateful. I like to tease them a bit and I’ll play with their cocks long before I undress or they do. It is amazing how men react when you reach down there and say, “Are you hard yet?” If they are not hard when you ask, they are thirty seconds later. First dates I go one round, blow job or a good old fashioned missionary style ride with none of the trimmings and a party hat. Once I get to know a guy my horizons expand and I am happy to do BBJs and doggy and reverse cowgirl. I become a porn star date but only when I know they are willing to pay to play.

I don’t like to talk about my actual income, but I never see a man a second time who does not bring a minimum of $750. Most of them quickly get the hint that $1000 plus a lovely gift and a tip will ensure I am available when next they call. I screen every man I see thoroughly and I never accept random encounters.

I am a bit snobby. If I was three inches taller I could model.  I much prefer wealthy, older men for who a $2000 dress is just the sort of thing a girl like me needs and which does not matter to their wallet. It’s great fun.

After college? I can’t imagine closing my little business until I get married. Why would I?

Rachel

Escorting the Hedgies

“As far as I am concerned I think if you are going to escort you should aim to make the most money you can as easily as you can. And that means lots of well off clients.” said Rachel in our Skype call.

We’d found Rachel via a referral from another escort who worked in Boston. This girl told us, “I think Rachel is the smartest escort I’ve ever met. She has the whole thing figured out and you should talk to her.”

Talking to Rachel is not all that straight forward. While she advertises her services online, all of her communication is carried on through her escorting website. So we wrote. And got no answer. We asked our friend in Boston to see if she could persuade Rachel to have a chat. That did the trick.

“I don’t really talk about my business.” said Rachel. “I mean I am an escort. I don’t pretend to be anything else. I sleep with men for money.”

We told her that her escort friend in Boston said she was “the smartest escort” she’d ever met.

“I am not so smart. But I am pretty good at figuring things out. I always begin any project by making a list of the questions I think will make a difference. With escorting the questions I came up with were: #1 what does a successful escort need?

The short answer to that question is a lot of well to do clients. Because there is no point being an escort for small money. Total waste of time really. And way too risky. The more money an escorting client is prepared to spend the less likely he is to be dangerous. Which is not to say wealthy men don’t have their little peccadillos and fetishes and obsessions – thank goodness because that is where the real money is, but I’ll get to that.

The point is that the wealthier your escorting clients the fewer problems you are likely to have and the more money you are likely to make.

Question #2 was a little more interesting. Where are all these wealthy men? Now the obvious answers – New York, Los Angeles, San Jose – think Silicon Valley – San Francisco, Seattle, Dallas, Boston, Palm Beach are all true. But every one of these cities and the others which come to mind have big downsides for an escort. Law Enforcement and competition are the biggest. Yes, usually law enforcement is focused on those poor girls on the street or advertising the $40 blow jobs; but in every major city there will be ambitious cops who will decide they want to take down a few high end girls. No thank you.

Competition is the other huge factor. In places like New York and San Jose and LA you have beautiful girls from all over the world chasing a limited number of rich guys who like escorts. Sure, the escorting rates in those big cities can be huge; but the number of girls working is also huge. Plus you have the “models” and the actresses who are part timing.

When I was looking at setting up my escorting business I quickly realized that the “obvious” place to run the business was not in a big, flashy, city with high rents and huge competition. Which lead to Question #3: If not New York or LA or Seattle then where?

Answering that question took a bit of research. Which was fine because I actually did a lot of research when I was doing my undergraduate degree.

And, I know you are dying to ask. I did go to a private college – I won’t say where – and yes, I did do a little sugaring and escorting in college but really just because I liked to have a fair bit of extra money and it was just so easy to put up a sugar ad or a one off escorting ad. But I really did not see what I was doing in college as a business. That came just a bit later. Which we can talk about.

The trick to setting up a research project is to ask the right question: in this case, where are there concentrations of well to do men? In the summer the year I graduated from college I set about finding out where these guys actually lived. Google is your friend and it was fascinating. Pay attention to Charles Murray’s great book, Coming Apart. Look for the Super Zips. I was living in the Boston area at the time and, given the choice, I really wanted to stay in the North East. But I did fly out to the West Coast to see Silicon Valley up close. No doubt at all that there was a lot of money along Sand Hill Road and I remember reading a great description in USA Today, “Silicon Valley is like a military base: There are very few civilian women and lots of money," said one Silicon Valley entrepreneur who spoke on the condition of anonymity because of the sensitive nature of the topic.”

Well, yes. The trouble was that the whole Silicon Valley area is stupid expensive to live in and there were a lot of girls who had the same idea. Plus, the San Jose police spent a ridiculous amount of their time trying to catch escorts both in the hotels and bars around Silicon Valley and online. I spent a couple of days there and then up in San Francisco and I realized that while there was a lot of money to be made, the risk reward ratio and the competition from other escorts made the whole place unattractive.

The other thing was I am just not that interested in nerds. I don’t play online games, I find Game of Thrones as unwatchable as the books were unreadable, I know how to use a computer but I don’t love my computer. Escorting is a funny business. You may not love all your clients but it sure helps if you like them or can find something in common with them. I didn’t have anything in common with the guys I met while I was in the Valley and I was not even working.

I looked at a few other areas but they all seemed to have more negatives than positives. My objective for my escorting business was to make and save as much money as possible. You don’t save money in a big city. The rents are too high and everything you do is expensive. So what I really wanted to find was a concentration of wealthy men somewhere I could get a great space for nearly no money.

Impossible?

It would be if you didn’t do your research. Do you know where the greatest concentration of hedge fund headquarters are in America? You might think New York and you would be close; but, in fact, all those financial engineers can do the math and they don’t like commuting so they started setting up shop in Fairfield County Connecticut. Which is the county closest to New York City and one of the wealthiest counties in the US. It has direct commuter connections to New York City – which is fun and useful for business.

I drove down from Boston. Taking the freeway it is an easy three hour drive. I booked an AirBnB room in the little town of Fairfield itself. Charming and just bursting with money. I spent a few days there just driving around and looking at apartments – pretty dire – and, to my surprise, houses. Here is the strange thing about a place like Fairfield County; there are lots of multi-million dollar houses and fifty million dollar estates, but there are also a lot of very private, out of the way houses, gate houses, boat houses and other small buildings which have been fixed up and then, in many cases, never used. I had not really thought about the potential of a house for an escort business but when I saw a really pretty little white clapboard house on the back of a lakeside property which had originally been the maids’ quarters I got to thinking very hard indeed. I rented it.

So Question #4: what were all those wealthy men wandering around Fairfield looking for in an escort?

When I first started sugaring and escorting in college I had a very simple routine. I knew my clients were looking for sex with a college girl and that is exactly what they got. I didn’t have many daddies and I didn’t see many escorting clients, but I saw enough to realize that there was probably a lot more a girl could do than just a quick blow job or twenty minutes between the sheets. But as I was really doing the college girl escort thing as a bit of a thrill, a hobby, I never went much further. Now I really wanted to figure it out.

My little house had three bedrooms, a very pleasant sitting room, a dining room and a kitchen. It had a small fenced yard and I had run of the 30 acre estate which surrounded the main house. The owners, a lovely older couple, were just fine with my story that I was trying to finish a book I had started in college and actually reduced my rent in exchange for my going up to check on the main house every day when they were away. My maid’s house was invisible to the main house and had a hundred yard gravel road coming in off a secondary road. It was private, not to say isolated. Which suited me. It was also partially furnished and the owners, who had a lot of everything, suggested I might like to take a look at some of the furniture they had in one of the out buildings. It was wonderful. Lovely old fashioned chintzes and nice, real, 19th century landscape paintings. It was easy to furnish the house in a certain style.

The thing I learned being a college girl escort is that men seem to like seeing girls who remind them of who they were in college. Girls like the woman they married but young enough to be their daughters. My suspicion was that there was good money to be made simply by recreating the world as it was twenty or thirty years ago.

Which lead to Question #5: which world? Thirty years back there was a pretty firm distinction between good girls – like their wives and daughters – and naughty girls who might be in the escorting business. Which side of that line did I want to be on? Or should I just offer the GFE and go with that?

It was not an easy question without data and the only way to collect data was to actually advertise and see what happened. I decided to try the good girl vibe. In a way it really was the only way to escort in Fairfield County because, if you walked down the street, they were all good girls. The younger women were nicely dressed and carrying Kate Spade or Tory Burch bags, the older women were really well dressed and carrying Hermes and Dior bags.

So I fitted in. There is no reason an escort has to dress like some sort of sex bomb – pretty lingerie is more than sufficient. My advertising and my website were all about a sort of naughty preppie girl who, in a temporary lapse of judgement, decides to give escorting a whirl. All with a hugely arch sense of humour. I even made a few hedge fund jokes.

Question #6 is the age old problem of what to charge. Charming as it is to say “as much as possible” the fact is that escorts have to set their rates according to the market they are in. But Fairfield County is basically a bedroom community for downtown Manhattan and a lot of the businesses in the area could just as easily be on Wall Street. New York escorts, who are almost always booked through agencies at the upper end, charge more for their time than escorts anywhere in the country. Which meant the men in my little market were used to paying top dollar. The problem was that the local girls seemed to think $400 an hour was top dollar.

For the hedge fund guys I wanted as clients, $400 was what they might spend on a tie. Just as importantly, setting a high price, but one which was lower than the agency prices in New York, meant I was signaling I was not like the other girls. It was a high risk, high reward strategy I thought would make my escorting business stand out for the right reasons.

I also decided to only do in-calls for first time clients. I loved my little house and I had decorated it in a very warm, very welcoming way. Because the house is very private we can enjoy ourselves pretty much anywhere which is great fun on those hot summer afternoons. I dress seasonally, pretty cotton dresses, usually front buttoning, in the spring and summer, knits, also front buttoning, in the fall and winter. But I will also just wear jeans and a sweater.

Hair and makeup are miles away from the more standard escort fare of slightly over the top. For day I wear a little lipstick and a bit of mascara, evenings some light eye shadow and a tiny hint of a bronzing foundation to set off my cheekbones. The lipstick is a little redder. I have my hair in a short, rather clever, bob which I can slick back if the client likes a bit of a dramatic, boyish, look but usually it is just wash and wear straight from the shower. No perfume. No scented anything.

My clients have a certain pattern. Saturday and Sunday afternoons are almost always booked with a client coming over for the length of a round of golf. We’ll usually have lunch and then adjourn to my really very sweet, very French country style, bedroom. I also see quite a few men between four and seven weekdays. They leave New York a little early and arrive home a little late. I do, at most three evening dates a week.

In an average week I will see between seven and ten clients. No rush. I charge by the date rather than the hour and most of the dates are a couple of hours long.

As I hoped, my advertising and website appeal to very affluent men. I joke about being a hooker to the hedgies but that is not far wrong. At least half my clients are in the hedge fund business. Which is great because, while they will buy their wives a Birkin to celebrate a killing, they will buy themselves an evening or two with me. Although one sweet man got confused and bought a Birkin for his wife and a Kelly for me. I know which Birkin he got her and I have seen her carrying it.

So, question, #7 as I recall – what do these wealthy men like? Well while there are certainly some hedgies with a few kinks – I have a nice selection of toys and strap-ons in a few, moderate, sizes – most are really looking for the thrill of a slightly illicit time with a girl they can trust completely. I stress discretion and my clients very much appreciate that.

Back in John Cheever and John Updike’s day these men would probably be having affairs with their secretaries or with the wife of a friend. Men who make 100 million dollar bets for a living tend to have very high sex drives but they also tend to marry smart, rather sexless, women.  Perfectly turned out but sort of dry, brittle. My escorting world reminds them of the girls they enjoyed in college but, mainly for social reasons, never really thought of marrying.

I am very much prim and proper walking down the street in Fairfield or Southport.  I look very much like my clients wonderfully polished daughters. After all, I went to the same sort of school and the same sort of college they do.

Outside the bedroom I am very demure. Prim. But with an edge. I’ll wear a quarter cup bra under a thin cashmere sweater so my client is pretty sure he can see my, often hard, nipples as I serve him tea or fix him a drink. Many of my skirts and dresses have cunning slits where my stockings tops show. In the bedroom I am just as demure and just as proper. My clients almost never see me completely naked and I am more than happy to pretend to be just a little reluctant at first.

Hedgies tend to be performance driven in bed and out. They want to break down a girl’s resistance and then go all “Master of the Universe” on her. Which is fine with me. I am always well lubricated and, honestly, I like sex a lot and I like being paid to have sex even more. Thinking of a shoe box full of hundred dollar bills gets me wet every time. So, I have no problem lying back and spreading my legs and thinking of the Benjamins.

But even when I have a millionaire eight inches deep in my pussy I keep up my ladylike persona. No “dirty talk”. No touching my backdoor. And, unless I know a guy really well, I don’t like having my pussy licked. It isn’t that I don’t like the act itself – done right it is lovely – but it is so intimate that I keep it as a treat for special clients. I am very enthusiastic in bed but I have very hard limits.

Lots of my hedgie clients like to get more than a little kinky. I did mention strap ons? But, like trying to buy a Birkin at Hermes, you have to work up to that. I will not even discuss kinks until I have seen a man at least four times. By then I know him and he’s invested several thousand dollars. On that fifth date I might test the waters a little with a well lubed finger up his backdoor. If he likes it then we can talk. Kinkiness, whether it is my wearing something special, foot worship, golden showers (for him, me never) or a good pegging, is always expensive, very expensive. Basically double or triple my normal rate. But by the time it even comes up I know whether I am dealing with a minnow or a whale.

My clients really like the fact I fit into their weird, upper class, preppie world so well. They don’t want to date models or girls who lack the refinement a good college education brings. As I said, they like the fact I could easily be their daughter or their, likely second, wife.

I don’t think my escorting clients have an incest fantasy going. Not specifically. It’s more about a sense of wanting the attentions of a pretty, well mannered, young girl who is delighted to accommodate their rutty desires in exchange for the one thing they have far too much of: money.

Which, of course, leads to question #8, how long will I keep escorting. When I first started in Fairfield, my plan was to work for a couple of years, build a nest egg and move on. Well, that was three years ago and my nest egg is growing fast. But I really have no intention of quitting a great, hassle free, escorting business. Maybe when I am thirty and look more like my clients’ wives than their daughters.

However, I do have one plan which I am working on: if I can keep a couple of dozen hedge fund managers happy I am pretty certain I could keep one delighted. So, very quietly, I have started looking around in Boston for a real live hedgie husband. And I do know that I would find more in New York, but just like escorting, the New York marriage market is stupidly competitive. Plus, almost all my Fairfield clients either work in New York or work with guys who do. Boston is a world away but there are still plenty of nice, wealthy, guys who are, though they may not know it, in need of a wife.

I am taking my time. Escorting in Fairfield, seeing my regulars, taking little shopping sprees to Manhattan, reading fills my days. I have created a little personal consulting business for cover and, soon, I’ll be escorting in Fairfield and consulting in Boston. Hedging my bets as it were.

Juliana

The Luxury Approach

There are plenty of escorts out there who promise to pamper, to be luxurious, to spoil their clients. After all, booking an escort is a luxury purchase and in a competitive market some escorts will try to cater to that end of the market.

At the same time we were amazed to see an escort ad which really sounded more like an ad for a high end spa than a roll in designer sheets.

We wanted to find out more and reached out to “Juliana” through her very attractive website. A website which looks, for all the world, like a modernist piece of art. All pale, beautifully faded pastel colours.

“I work in San Francisco.” said Juliana in our Skype call. “My clients are younger, usually very successful, totally driven guys who are pathetically stressed.”

Juliana had set her Skype up so that she could use a DSLR to shoot her video and this mean we could see both her and, in the background, her astonishing apartment.  She didn’t advertise her age and we didn’t ask, but at a guess she was a very well taken care of early thirties something woman. Her honey blond hair was cut in an asymmetrical bob and she was wearing a pretty, pale grey, light knit dress. Very red lipstick and natural, but present, make up.

Behind her we could see an enviable apartment with sun streaming in through tall windows and modern black leather and chrome furniture. It is a pet theory of mine that the size of a space matters less than how high its ceilings are and Juliana’s apartment looked to have, at minimum, fourteen foot ceilings. All painted a honey taupe with black framed, large, fashion photographs stacked on the walls cleverly.

Juliana spoke with the sort of assurance one expects to see in a lawyer or doctor. Full sentences, no slang, careful diction: all in a rather soft voice which seemed to come from a very deep, very calm place deep in her chest. A chest one could not help but notice, graced with braless breasts which were larger than one would expect on such a light, lithe, frame.

“The last thing in the world my clients want is a lot of over the top sexual stimulation. Really just the opposite. But it took me a while to realize that.”

“I didn’t start escorting in San Francisco. I really started in the alt sex work scene in Portland. You know, Suicide Girls and the only vegan strip joint in America. I’d finished my undergraduate degree at Reed College so I was dug into the whole Portlandia thing. Which was fine and it was a graceful introduction to what the lumberjack shirt wearing girls call “sexwork”. It was all surprisingly innocent and I had my first date with a software executive with a sleeve of tattoos and some sort of complex about wanting to help girls like me. Which was actually pretty funny because, of course, in order to save me he seemed to need to see me once a week and, as he was there anyway, a blow job was not out of the question. Men!

The problem with the sex work scene in Portland is that there was not a whole lot of money in it. Or at least the way I was doing it. And, honestly, I’d been in Portland for nearly a decade and the novelty had worn off. I’d always loved San Francisco. Beautiful, very much a great city and the center of the tech universe. But it was really expensive.

I did a bit of scouting online and I thought there might be a market for an independent escort who came at the escorting business from a luxury perspective. I had some money saved from my Portland business, not a great deal but enough that I could rent an apartment and buy a bit of decent furniture. I drove down to San Francisco one weekend and looked around at apartments. Wow. I knew it was expensive but this was crazy. I’d wanted a two bedroom apartment, one bedroom for work, the other for my actual life. No chance of that I realized looking through Craigslist.

I have to admit I got pretty depressed looking at $4500 a month 750 square foot boxes. I was staying at an AirBnB spot near downtown and I came home the second day looking pretty glum. My host, a wonderfully festive old queen who had bought back in the 1970’s was waiting with a big glass of chardonnay and some appies. We sat on his roof deck overlooking the city. I told him about my house hunting disaster.

“Well, do you like where you are staying?” he asked. I told him I did. “Well why not rent it?

I explained to him that the nature of my work made privacy pretty essential. “And what do you do?” It was a big glass of chardonnay, almost gone and I told him. “Good for you dear. I suspect there is a big market for girls here. There certainly is for boys.”

We did the deal on the spot. Basically I got the bedroom and living room I was staying in plus the private bath and another room which I am in now which is just off the living room. No strings attached and half the price of the places I’d been looking at. And, the best thing, it was totally furnished with just the sort of modern furniture I was planning on buying. I paid the deposit, drove back up to Portland, had a garage sale and put what was left in the back of my car. I drove back down to San Francisco along the coast highway because I had five days to kill before

Every escort I have known has a working name. I wanted mine to be a bit romantic, soft and feminine. But I wanted more than that. The girls I knew in Portland who escorted usually were pretty much the same girl escorting as they were in their straight lives. Which is fair enough but not what I wanted to do. Or, more accurately, I wanted “Juliana” to emphasize certain elements of my own persona in an escort setting.

While it was not a popular position in sex work in Portland, I like to spend my time in a feminine, sleek, expensive environment. I like well tailored clothes, a great hair cut, careful grooming and a sense of gliding into a room. Portland sex work was more feminist than feminine and that always made me uncomfortable. My sense was that there would be a market for a really feminine, stylish girl who went out of her way to create a very safe, very unstressed, environment for her escorting clients.

Most of all, I wanted my prospective clients to really “get” how luxurious a few hours with me was. And it was that luxury which I thought would sell my escorting services.

From the very beginning I wanted the consenting adult activities to be a part of a much bigger package. Girls will talk about the “Girlfriend Experience” which I get but it’s not really what I wanted to offer my escorting clients.

I wanted to give very driven, busy, stressed men a break, a pleasing pause in their lives. To do that I wanted to change up the escorting business model a bit. As economists would put it, escorting is pretty much defined by its “transactional” nature. Bluntly, the client gives the escort money and she gives him a good time. This business model was what I had used in my Portland sex work. Now part of the reason the transactional model is used by escorts is that they see each encounter as, essentially a one off deal. Even with their “regulars” each encounter has to be seen as the last encounter. As I drove down the Coast and into the redwood forests I realized that this was not the only model which would work.

Wealthy men have had mistresses pretty much since the beginning of wealth and less wealthy men – or cheaper ones – have sugar babies they keep on an allowance. I was very definitely not the sugar baby type largely because I really did not want to see the sorts of men who “kept a side piece”. I had no objections to being kept as a mistress. In fact, in my notebook I had a separate page for “mistress”. But was there something in between being a girlfriend experience escort and a mistress?

I thought I had a potential solution. Keeping a mistress is a big commitment and one of the reasons men see escorts is to avoid any commitment. But what about what amounted to a time share mistress arrangement. Basically, instead of selling dates one at a time, why not sell a block of time, say three months, with an evening a week and the occasional afternoon of fun as part of the package? Not for every client but as an option.

The other thing I thought would work in the bigger market of San Francisco was the idea of a flat rate, no time limit, date as the basic way I sold my escorting services. Yes, that would limit the number of clients I could see; but if I set my rates high that would not matter and, in fact, I was a lot more comfortable being a low volume provider.

Given what the guys in San Francisco were apparently able to pay in rent, my business model assumed six high end clients a month with one or two invited to participate in my “time share” mistress idea. But I left that idea out of my escort advertising.

In fact, I left any reference to escorting out of my advertising. Instead I advertised as a stress management consultant. “Experience the healing arts of a beautiful woman in simple, modern space. No time for a girlfriend, driven by your success? Find out what you are missing without the added stress of a relationship. I never text, I never call, I don’t need you to either. I am just here. Ready, beautiful, relaxed when you need me.”

I had a great picture from a fashion shoot I’d done for a friend a year before. Me in a really pretty jacket, no top, looking side long into the camera. Fashion forward, modern and my favorite picture. And it had the virtue of looking like me, but only from a certain angle. I wanted to keep my escorting very discreet.

So, I got to San Francisco. My lovely landlord actually baked me a cake with the wonderful line “Welcome Strumpet” in bright red icing which matched a kissy lip print. I settled in and put my ad up. I did use escort advertising sites but I also put the ad in print in a couple of the entertainment guides. Because it was not at all “escort” they were happy to run it under personal services.

I set it up so that to contact me you had to go to my website. I learned a lot about screening when I worked in Portland and I really wanted to see only escorting clients who were willing to be up front with me. With the internet it is amazing what you can find out and confirm with nothing more than a name and a location.

I post my “all in” price and a couple more pictures. Plus, I have a couple of really nice shots of my space with some fresh flowers. It is all designed to look really inviting and calm. Again, something which I learned in Portland is that while some men are seeing an escort for the sheer excitement, a lot of men are there for a break. Those were the ones I wanted.

So, a few hours after I put my ads up I had five or six queries and two of them seemed to be men I would like to see. So I made arrangements and, before I really knew it, I was getting ready for my first appointment as a San Francisco escort.

I am a girl who likes dressed and skirts and tops. A long high collared lightweight knit dress, like the one I am wearing right now conceals and reveals at the same time. I know I have a small frame and surprisingly large breasts. And yes they are natural. The right knit dress, a clever lacy, unpadded, balconette bra and a silk chemise and I am temptation itself. Switch over to a full cup bra and I look elegant and very much a lady. Which is, frankly, how I always present for my appointments for first time clients. Part, but only part, of my service is sexual and it is not a given on a first encounter. There have been a couple of clients who, frankly, were just not at all plausible for consenting adult activity when it came to the crunch. And I tell my clients up front that this is a possibility. The ones who blow me off when they hear that are doing us both a favour.

I am also a girl who figured out her make-up, hair cut and skin care years ago. It really does only take me twenty minutes from a standing start to get ready for an incall escorting appointment. But, and this is huge, in fact I take a couple of hours most of the time because I want my space to look wonderful and I always have a few appetizers and some nice, fairly low alcohol, wine to serve. Then I make sure there are fresh really great towels in the en suite and beautiful clean sheets on the bed. Flowers of course. And, if it is evening, candles.

My clients feel like welcome guests and, eventually, friends, who are stopping by for a bit of conversation and relaxation. Nothing is hurried. When it is time to move things along I’ll usually have my client unzip the back of my dress and lead him to either the en suite where I have run a bath, or directly to the bedroom.

There is very little about pleasuring a man I don’t know but the actual fact is that most of my clients, after a little gentle teasing, simply enjoy a willing, gentle partner who apparently enjoys herself as much as they do. I suspect that is the real secret to the escort’s art. Bathing a man, with lots of unscented bubble bath, is incredibly relaxing and erotic all at the same time. Once in a while I will actually give a client a soapy hand job and then rinse off his cum. Other times I will strip naked and join my client in the tub.

In bed I am really all about taking lots of time and really going deep. I don’t mind sucking a client’s cock, on and off, for half an hour and edging him. But I also love it when a client just can’t wait and wants to fuck me immediately and hard. I will urge him on and then, when he has relieved his unbearable urge, I will lie with him and bring him back so he gets hard again and can enjoy my pussy more gently and completely. My clients think it is all up to them but, really, everything I do in bed I control. I often come for real with my clients but I am very good at the minor art of orgasm faking if necessary. Happily, whether I come or not I am a very wet girl naturally so I am able to enjoy being fucked just for the pure sensation.

I saw three clients in my first full week and one of them became my first “time share” mistress client. He loved the idea. The way I worked it out was that my time share client would pay me monthly for an agreed number of visits, usually four or five. I discounted my time a little for this arrangement but what it really did was remove the whole “transactional” element which makes conventional escorting seem more than a little cold blooded.

Because I knew I would be seeing my time share mistress clients more regularly than ordinary escorting clients, I really got to know them. Eventually I had four which was pretty much as many as I could service. All in, that was about twenty encounters a month so there was not that much time left for regular escort dates. But, as any clever mistress will tell you, it pays to be looking for the next patron so I kept my stress management ads running.

I did, however, raise my rates. A lot. What I had not realized about San Francisco was just how much money these guys had. There was a reason why there are a lot of $10,000 a month apartments on San Francisco Craigslist: these guys can afford it.

I realized that one of the main ways of choosing an escort if you are really well off is to assume that, like fast cars and great red wine, price is a pretty good indicator of quality. These were not guys who read hobbyist reviews. Quite the opposite, it was a feature that I had no reviews. In fact, it was a feature that I presented myself in my ads, on my website and in conversation as barely an escort at all.

The greatest luxury of all turned out not to be the fluffy towels or the honed oral technique; it was the illusion that a really pretty, elegant girl wanted to spend time with an otherwise harassed, stressed and wildly busy guy. Whether it was a straight escorting date or a time share arrangement, I tried to keep the whole money end of things very much in the background. Of course I like my envelope but I try to leave my clients with the impression that I enjoy my time with them regardless of the money.

That impression is, in fact, true. Unlike my escorting in Portland, in San Francisco I created a business which was very exclusive. The men I see, especially the men I see on the time share basis, are actually men I would probably date. No, it is not the Pretty Woman scenario with the billionaire white knight on a charger, just nice guys who, realistically, don’t have the time for a real relationship. For them, while I am an escort, I am also that great girl who does not need any maintenance at all.

The real luxury for these guys is having a break from making decisions and inventing the future. Most of my clients are a little older than I am but I have two who are younger. What they value is being able to sit for a little while, sip some wine, have a few nibbles and know that if they turn their phone off – which I insist on – the outside world is on hold. Of course they enjoy the consenting adult activities but the reality is they enjoy the break even more.

Trish

Mile High Escort

We were looking through some escort ads the other day and were struck by a pretty girl in Denver Colorado whose picture seemed to jump off the page. It was not that she was particularly striking to look at, there were more beautiful girls on the page, but her face has a certain welcome which is very hard to miss.

The copy to the ad was equally inviting in a fresh, sunny, very gentle way.

“I love what I do. I take wonderful care of myself and I would love to take care of you. No hurry, gentle with a deliciously wicked streak. Let’s chat.”

So we did. By Skype. “Trish” turned out to be twenty seven and just as bubbly as her ad had made her sound.

“I really do love what I do. I have a nice clientele, about three quarters regulars. I don’t run my ad all the time. I will put it up when I have a few blank days the next week. They always fill up.” said Trish pushing her honey blonde hair off her face.

“I like men. I always have but, to tell the truth, when I first got into the business I did it all wrong. First off, I got into the business because I was desperate for money. Which is not a good place to start. Second I wasn’t in Denver, I was in LA. LA is a very tough town to escort in much less start escorting in. Super competitive with all those wannabe movie stars and those porn star girls who escort on the side. So you have to use an agency which is a whole other mess. I was with three and two of them didn’t pay me what they owed me as soon as they found out I was leaving.

Working with an agency is not at all for me. I needed the work so I did it but I hated all the politics. The bookers knew who the good dates were and they gave them to their friends. I got either random guys the agency had barely checked or known goofs. Not dangerous but not a heck of a lot of fun either. Plus, the one agency which I stuck with was crazy about time. They would “fine” you if you went ten minutes overtime. It was awful. But setting up as an independent in LA is crazy expensive because if you do in calls you have to have a nice place which is money. If you do outcalls you either have to have a car or you take a cab which takes forever and is crazy expensive and then, when you leave, you have to find another cab and that can take hours. At the end of six months I was a wreck and I was still pretty desperate for money.

I guess I had a bit of a breakdown. And I got careless. I was OK but I got one of those dates which just creep you out. It wasn’t what the guy wanted to do, that was pretty ordinary, it was just how much he wanted to verbally abuse me while he was doing it. Just nasty, creepy stuff. I got out in one piece and I didn’t get out of bed or answer my phone for three days. And I forgot I had an afternoon date with one of the few regulars that I had managed to sneak past the agency and he knocked on my door and I was a total, kinda smelly, mess.

What a nice man. He took one look at me and said, “OK, off you go to the shower, don’t bother with makeup, put your hair in a bun and I’m taking you to lunch.” Saved my f’ing life. No, really. I didn’t know him that well but it turned out he was an executive recruiter. “I see this all the time. You hit a wall.” he said in a nice restaurant which was half empty at three. We talked for a couple of hours and I felt a little better. I figured the least I could do was invite him back to my place and do my best.

“Not a chance.” he said, “You are taking a few days off escorting in LA. Call your agency. I’d suggest you simply quit but up to you.” I quit. At least they didn’t owe me any money they could stiff me for. While I was calling he was on his phone.

“So, here is what we are going to do.” he said and I nodded. “We’re going to Denver. LA is a terrible place to escort and you are showing all the signs. Time for some Rocky Mountain air.”

I grew up in the Valley. I’d never been out of LA and the whole thing seemed like a dream. I wasn’t arguing. “Anything at your apartment you can’t live without? Cat? Goldfish?” There was nothing. Not one damned thing. After six months of escorting I had a second hand couch and a bed which was way too hard.

“OK then” he said, “I’ve cleared my schedule. Time for a road trip. We can swing by your apartment for you to pick up a few things and then mine and then we are off.”

I have to admit I really didn’t care where I was going. Or what I was going to do when I got there. Somehow David, that was his name, seemed to have everything figured out. “We’ll take Highway 15. We’ll stay overnight in Barstow which is not a huge drive and then see how far we get tomorrow. If you decide you don’t want to go to Denver we can turn around in Barstow and be back in LA by lunch.”

Which is what we did. Drove out of LA and through the Valley. We didn’t talk much on the way to Barstow. I just sat in the passenger seat and thought about what the hell I was going to do in Denver. Before I figured that out Dan was pulling into a motel in Barstow. We dropped our bags and headed out to an Italian Restaurant.

“So,” said David when our meals had arrived and we had a bit of privacy, “Do you like being an escort?”

It was a question I really had not considered. I escorted because I needed money and this seemed like the best, and maybe only way to get it. “Not really.” I said. “Well, actually, I like the actual escorting part of it. I like meeting new guys and I enjoy being able to give them a lot of really intense pleasure. It’s all the rest that I don’t like.”

David was, and is, a really good listener. He knows how to get people to talk about themselves. Maybe because of being an executive recruiter. By the time we’d finished dinner he knew more about what I hated about escorting and what I liked about it than I did. As he paid our bill he said, “There is a lot here to think about. We can talk about it in the morning whether we are driving back to LA or on to Denver. I want to think a bit about what sort of game plan is going to make sense for you going forward.” He said things like “going forward” and “game plan”. That was his world.

It was funny. When we got back to our hotel room he was very shy when I suggested a few consenting adult activities. I finally had to put my foot down. “You are working really hard and spending a lot of money to give me a new direction. I am a professional and I want to make sure you are well taken care of.” There are very few men, no matter how nice, who turn down that sort of offer from a girl kneeling in front of them in nothing but her bra and panties unzipping his pants. I sucked his cock, no condom, until he came in my mouth and I swallowed every drop of his cum. All the while looking right up at him like the desperate, dirty, little slut I was sure he thought I was. He went to sleep with a smile on his face.

The next morning, after I attended to the morning wood David, like most men wakes up with, he said to me. “OK, Denver or back to LA?”

“Denver.” I said without a second’s hesitation.

“Escorting?”

“I think so. I mean I could get a straight job but doing what and for how long?” I said. The fact is that I had very little training and had spent most of high school perfecting my outfits.  I never really learned how to work.

“OK.” said David. “We’re off. We’ll get breakfast down the road. I’d like to get some miles covered if that’s ok with you. We can pick up coffee on the way out of town.”

There is a lot less traffic in the early morning on Highway 15 between Barstow and Las Vegas. We sipped out coffee and drove through the high desert. Fortunately it was late Fall so it was not super hot. David liked to talk and I was all ears because he was talking about what actually made a successful person.

“It does not matter what you are doing. You can be working in a Wal-Mart or running a big company or escorting. It is what you bring to the job. Honestly, it really is all about attitude.”

It is only two and a half hours from Barstow to Las Vegas and we postponed breakfast until we could hit an amazing “Best Breakfast in Vegas” restaurant. It’s funny, I grew up all of five hours from Vegas and had never been there. David had been there dozens of times and he grew up in Kansas. About 2000 calories later we were back on the road. But not the direct route to Denver.

“I’ve always wanted to see the Grand Canyon. We’re not in any hurry, at least I’m not. Let’s go.” So we did. We drove all the way down to the North Rim and it was amazing. Then we took our time driving quiet two lane highways which stretched across miles of high plains and through these amazing National Forests. Places I had never even knew existed. A lot of the roads we took would have been snowed in during the winter which was not far off.

We stayed overnight in Moab. By now David and I were really comfortable with each other. We could play a little and I am afraid we shocked the nice ladies at a cute little consignment store where David wanted to buy me a few clothes. David is certainly a gentleman but, well, I did mention I loved the consenting adult end of escorting and part of that is teasing. He was well and truly teased.

The secret to a great tease is, believe it or not, a full slip. And in the Moab consignment store they had one, beautiful, black satin slip with a zip on the side. I wore that and nothing else to try on my outfits and, to David’s delight, my nipples kept slipping out and once in a while my cute little bum would peek out when I was pulling a dress over my head. Too bad they didn’t have any stockings.

Over dinner David talked about setting up a really excellent escorting business in Denver.

“Here’s the thing. What you told me you hated about escorting in LA was all about bad planning and not really thinking about what you like doing. You like the actual escorting. Seeing men, being paid for your time and your talent. There are lots of men in Denver but to really make a go of it you need to have a sustainable plan for not just your escorting business but the rest of your time.”

“In LA, between dates, you sat in front of a TV or a computer screen. You were waiting for the phone to ring because that’s what you thought escorts did. And, I suspect, that is in fact what most escorts do; but they don’t have to. You told me that most of your appointments were in the late afternoon or evening. So, in Denver, why not simply say that you only book appointments from four o’clock to ten o’clock. That gives you your days to yourself.

Escorting will give you the income to do other things.”

“Like what?” I asked.

“If I were you I would look for two things: first a part time job and second something to study which will give you a credential you can use to get a better job. It seems to me that “just escorting” does not suit you at all. You need much more going on. Do more.”

We finished dinner and went back to our hotel. I tried on a few of the things David had bought and, as you might guess, that teased him all over again and we had a delicious round of consenting adult activities.

He was up early and on his laptop. “We have to get going. I’ve found you two furnished apartments to look at.”

“But I have no money. Like $50.00.”

“Yes, but I certainly didn’t expect you to go on this road trip for free. You’ll be fine.”

And I was. It was funny to watch the landlords take one look at David’s watch – which really was a gold Rolex – and his car which was German and very sleek and quickly conclude that he was renting the apartment for his mistress or girlfriend. I guess I looked a bit like a mistress because David had bought me a really pretty Ralph Lauren dress which was very body conscious. Very. And it didn’t hurt that he paid the security deposit and first month’s rent on a Platinum American Express card. He used the same card to get me a smart phone and a cute little laptop computer.

We had great fun shooting pictures of me using the phone camera. David was a bit of a computer whiz and in an hour he had a gorgeous website put together on my laptop which he showed me how to update. When it came to putting up prices David asked me what I wanted to charge. Of course I didn’t know. He put in an hourly rate which seemed crazy high. “You can always go down.” he said. “But the sorts of clients you want are not going to blink at a little less than they are paying their lawyers. Escorts are way more fun than lawyers.”

We drove around Denver a bit. I could really feel the altitude. It is not called the mile high city for nothing. David stayed the night and, in the morning went out on his own for an hour. When he came back he had an envelope. In the envelope was $1000 and four prepaid Visa cards.

“Well, time to be headed back to LA. This will get you started. I’ll be flying via Denver pretty regularly so, if you need anything…” he kissed me on my cheek and hopped in his car.

The next day my ad went live. Pretty much the ad you saw. With a main picture David had taken of me standing looking over the Grand Canyon. Nothing terrifically sexy and probably the very opposite of what most people would think an escort would look like.

I have to admit I was a bit nervous. Would anyone call? But, I had my rent paid and some, well to me, quite a lot, of money. More importantly, I had just seen some of the most beautiful places in the US. Because David liked photographing me, I’d stripped naked and briefly, very briefly jumped into a crystal clear pool fed by a mountain stream with the Rockies as my backdrop – and yes it was very, very cold. I had a new world and a new life and I was not going to screw it up.

One of the things David had said was that I should take my time and be really, really picky. Which was amazing because I really had never thought of escorting that way. I’d thought that a girl would make the most money if she took every date. That’s what the agency told me. But David pointed out that without the agency and with my new prices I would make lots of money with five or six dates a week. “Why work hard when you can work smart? The guys I recruit can work very hard if they have to, but they rarely have to because they are thinking all the time.”

I took a little time to figure out which were the better hotels in Denver and I had a nice time checking each of them out. My thinking was that I would prefer to start with outcalls – until I found the best location for an incall – and if I was going to do outcalls I only wanted clients staying in really good hotels. David had insisted I buy a couple of really conservative pieces in the consignment store. “But I look like a frump.” He just laughed.

I realized he was right when, dressed in the frumpiest, least “escort” looking outfit I had I had an early drink in one of the hotels. I think there may have been a couple of working girls at the bar but I took a book and sat at a slightly secluded corner table. It didn’t take long for a rather chubby 50 something guy to offer to buy me a drink and two hours later my cash reserve was replenished.

All the while my phone was clicking discreetly with emails and texts from would be gentlemen callers. It had a clever notification light system I eventually learned how to use.

I was in business. I was escorting a completely different way. When David flew into Denver three weeks later we went for dinner. “Mountain air agrees with you.” he said.

He was right. Somehow moving to Denver changed how I looked, how I felt, how I did my escorting business. I even had a part time job. Nothing fancy. I was working retail at a cute little consignment store in a nice older part of Denver.

That was nearly five years ago, forever in escort time. But I don’t live in escort time, I have my life and a part, a small part, of it is escorting.

Sybil

Lesbian Experience

In the gay male world escorts and paid for encounters are simply part of the scene. It is not a particularly big deal and a surprising number of gay men have, at one time or another, been escorts.

In the lesbian world things are a bit more complicated and the edges much blurrier. For example, straight female escorts, from time to time, are hired by women. Or couples. While they certainly engage in girl on girl activities, it is not all that clear that these encounters would count as lesbian escorting.

The emotional and erotic world of women is a more complicated place than the male homosexual world or the heterosexual world. But we were interested in exploring how paid companionship works between women and looked around for escorts who lived in that world.

“By inclination I prefer sex with women.” said Sybil a very pretty, willowy, brunette in what looked like her early thirties. “When I was younger and just starting out as an escort most of my dates were with men and that was fine. Men are very basic and most will not even notice if you are a bit distant. In fact, most men prefer an escort to be pretty self-contained and for her to simply get on with the business at hand.”

“But even early on I had a few escort dates with women and they were completely different. Completely. I am what the popular press would call a lipstick lesbian. Very much the Portia de Rossi rather than Ellen. I love dressing up, putting on lots of pretty make up and really sexy shoes. One client of mine calls me her “style queen” which is pretty accurate because I am completely into fashion. I mean one of the reasons I escort is to be able to afford to buy really lovely things. If I want a $7000 “it” bag I don’t want it next year, I want it now.”

“I lead a sort of nomadic life. I have a house I bought a few miles out into the desert hills near Santa Fe New Mexico. All very arty and Georgia O’Keefe; but I like to spend a few months at a time in decent sized cities on both coasts. Escorting lets me do that.”

“Over the last few years I have shifted my advertising and my website to be much more lesbian or, more accurately, female friendly. When I was younger I had an escorting clientele which was 80% male, now it is 80% female and, to be honest, I really only see men who have been clients for years.”

“I could spend a lot of time talking about the differences between male and female expectations for an escort – and they are huge. But the expectations are only one side of the equation, the dates themselves are night and day.”

“Men appreciate a nicely dressed, well made up, pretty “hair and nails” girl but it is all very much preliminary to the main event which, usually, takes place between the sheets and is, ultimately, what the gentleman thinks he is paying for. Women are completely different.”

“Most of my women clients come at the whole thing very differently. They are looking for connection.”

“In my experience, women who want to see an escort come in two very distinct flavours: the first are women who like girls, know they like girls and are pretty open about it. The second group, and they are about half my clients, think they might like girls, or have experimented a bit with girls and liked it, or are married but missing something.

The women in the first group are usually a lot of fun. They have usually come to a place in their lives where they enjoy other women’s company and the frission of excitement knowing that the evening will end in bed. But, and here is the thing, it is very much an evening. We’ll meet for a glass of wine, perhaps have a light dinner, maybe go to a lesbian club a bit later and then, likely after a nightcap or a dessert, we’ll end up under the covers. Nothing happens quickly. I am not sure it would even be possible to be a high volume lesbian escort.

The women in the second group – the experimenters, the girls who had an experience in college and want to try it again, the wives who are pretty sure that something in their marriage is not quite right, are wonderful. For some of them simply calling me is a hugely important step in getting their lives in alignment with their sexuality. Now, I hate the whole idea that escorts can or should be therapists. But I think the mere fact I am available to these women is therapeutic. And, frankly, so do my out lesbian clients. In fact, I have had women who were uncertain of their real sexual identity referred to me by those lesbian clients.

In a very real sense I am the safe place for women to explore the feelings of attraction they may be feeling for other women. If you are a nice Human Resources manager and a soccer mom and you suddenly find yourself really hot for another girl it may be a good idea to see if you even like sex with a woman before you take the risk of opening up to that girl. Along the way you may discover that women’s sexuality is somewhat less binary than male sexuality. Or not.

Of course some women, whether long term lesbians or experimenters have a real problem with the whole escort thing politically. There is a certain streak of anti-sex feminism which sees escorts as inherently victims of the patriarchy even if they are seeing women almost exclusively. It is really annoying frankly because these women want to see me as some sort of symbol rather than as a woman with her own “agency”. Now, that anti-sex streak of feminism is, mercifully, dying out but I still have heart to heart conversations with some clients where they are trying to convince themselves that I do not lack agency even though I am an escort. It seems very odd.

On the other end of the spectrum, I escort more than a few women who are, quite frankly, bored to death with the more caring and sharing sexual paradigm embraced by progressive lesbian couples. They want the intensity and the anonymity which often characterized the bar scene when they first came out. Which is a world which I really did not play in, but I can enjoy it if that is what my client is interested in. I will never manage the full on “bull dyke” or various other butch personas but I love getting into skin tight designer leather with my vintage ‘80s Claude Montana short black leather jacket and a pair of sky high heels and do a semiserious domme impression with a client. And, yes, at some point in the evening she probably will be up against a wall with my hands in places nice girls won’t normally want them. And, yes, later I might well tie up my client to “Constant Craving” and leave her gasping.

One thing the majority of my full on lesbian or experimenting clients really enjoy is a degree of glamour when they see me. For some of my clients glamour is part of their business – art directors, women who style or photograph fashion shoots – and they appreciate how I look because they know what it takes to look as glossy as I do. For other women, how I look, walk, dress and even speak is a path they might have followed but didn’t. There they are in their office drone pantsuits or the not terribly flattering outfits women lawyers seem to insist on wearing in order to look serious and across from them is a pretty girl in a dress and stockings and, perhaps, gloves. When I am out with these women I always look like “the girl” because I will be wearing a pretty, low neckline cocktail dress or a full skirted dress with a bustier top. Because, unlike when you are on a date with a male client, with a female client you can look very tarty – in an up market sort of a way – without anyone raising an eyebrow or thinking, “Well there is an escort.” Two women having a drink together, even touching affectionately, does not really arouse any interest at all. Or at least not negative interest.”

“Ultimately, though, the difference between a lesbian escorting experience and a straight one lies in your client’s need for connection. I am not saying my male clients don’t care who I am. They do, or at least most of them do. But, when it comes down to it, the men are hiring a girl for a particular purpose and “getting to know her” is not that purpose. And men are remarkably oblivious to the things women pick up on just sitting down for a glass of wine.”

“Remember I said one of the reasons I like escorting is that it lets me buy pretty things like bags. As you might imagine if I carry a Prada or a Celine bag on a date there has never once been a man who has said, “What a lovely bag.” For my female clients my bags are a point of entry. They want to know what bag it is, where I got it, why I picked this colour rather than that one. A male client might take me shopping and spend several hundred or even a couple of thousand dollars on me. But he does not “go shopping with me”. I have a few wealthy female clients who love nothing more than to go to lunch and then hit the stores. We shop together. Yes, she pays, but often we will buy more for her than we will for me.”

“Most of my female escorting clients are pretty well off. And most of their money is discretionary. While some have children, the majority don’t so they don’t have college and school and family vacations to worry about. If they are partnered it is often with a woman who makes just as much money as they do. Which means my female clients can afford to book much longer dates. I discount my rates a bit past three hours and a lot of my female clients will book five. Why not, they can afford it.”

“Not, of course, the experimenters. Those women are often counting every penny and get really worried if we go over time. I never worry. I enjoy my escorting dates and watching the clock is not part of the enjoyment. Letting a shy woman touch places she has kept hidden for twenty years is wonderful and deeply rewarding. For some of them, hiring me was a way of coming out, for others it simply scratched an itch. With my experimenters the escort dates were not usually as long but these ladies would come back, often a couple of times in the first couple of weeks and then somewhat regularly.”

“My more “out” lesbians have also become regulars more often than not. But, even there, the regular female client is so completely different from the regular male. One of the biggest things for my female dates was the fact they could go out with me and not worry about my becoming emotionally attached. Over a number of dates we’d become “girlfriends”. Girls who liked to spend a few hours together once or twice a month usually over lunch, coffee or drinks and then back to either her place or mine.”

“The regulars really do become friends. Again, the difference between men and women. Men are delighted to see me but, if I moved to another city tomorrow, they would find another girl. With women after a few dates there is a real connection apart from the escorting. I think a part of that is social. I don’t think it is any secret in parts of the lesbian community in my cities that I am an escort. I also don’t think most of the more successful lesbians care all that much.”

“For my partnered and now, sometimes, married clients, I am very much a safety valve. A little spice to keep things hot. In fact I have one couple who see me separately every few months. Each knows the other is seeing me and as one of them said, “It’s like a rebirth of our own bedroom lives.” I like that a lot. It is silly to generalize about any group of people and even sillier to generalize about “lesbians”; but I think a lot of lesbians are much more open to the idea of escorting than straight women. They don’t feel threatened by a young, glamourous girl because they have their own really solid relationship.”

“Probably the thing which I value most about my female escorting business is that openness. I am often invited to client’s parties, not as an escort, but as an interesting woman in my own right. That does not, and cannot, happen with my male escort clients because it is basically impossible to explain a pretty young single woman who you don’t actually work with. Lesbians don’t seem to worry that much.”

“The part that is hard about lesbian escorting is the same part that makes it easier – the women I see want to actually know me. They want to get past the escort wall and into the hidden garden. Where the men will, literally with a sly grin, ask “How did a girl like you get into a business like this?” and be very happy with, “This and that and then less of this and more of that.” my female clients get a bit obsessive. They really do want to know why I escort. When I tell them “For the money.” they dig deeper.

I spent one escorting date with a woman who, along with many other accomplishments, was a PhD psychologist. She really, really wanted to know. So I told her. I explained that by escorting I was able to make the money which let me led a very simple, deeply refined life where I could read or go to the Museum or afford tickets to the Opera or indulge in my taste for really pretty clothes and bags, keep my house in the desert and live in two cities. I was telling the truth but she was not buying it.

“Don’t you get a terrific sense of power, of giving, of intimacy from your work?” she asked.

“Perhaps.” I replied, “But I really like the fact that I am an escort. That my time, my body, my skills, my pretty dresses and lovely lingerie are appreciated. That women, and men, pay me for my time and my company. Escorting empowers me.”

“All she did was smile. Which was as annoying as Hell because her smile implied she “knew”. What she knew I don’t know. I do know that she had a wonderful time and has been back to see me half a dozen times without the “Why do you escort?” question coming up again.

“Law enforcement? Don’t be silly. My ads and my website are brilliantly vague. Coded for lesbians but interesting to men as well. But they are all designed to leave a police officer wondering if I am a companion, a therapist or just plain friendly. Escorting does not come into it. My ladies and even my gentlemen can read the code. I suspect most police officers can too but the whole gay thing is too politically fraught for them to really want to set me up. Or at least that is what a client and friend of mine who is an assistant DA tells me. So I never worry.”

I’m not actually sure how long I will keep doing the lesbian, or really anything, escorting thing. Many of my clients at twenty or thirty years older than I am so I suspect I could keep going for years. At the same time I keep getting great job offers from clients. Usually no strings attached. But if I took a job it would mean an end to long lunches and early cocktails and living where I want to. Escorting, at least escorting my way, is a life I am used to and I am good at.

If I had to guess I suspect that falling in love would end my escorting career. I have dated more than a few women and a couple of men on a non-professional basis. I’ve tried it both ways: where I tell them that I escort and where I am vaguely a consultant. The men seem fine with the escorting thing. Excited even. But it is a huge issue for the women. Not because they are particularly judgmental, they aren’t; but they cannot imagine how a relationship with an escort, even an escort whose clients are mainly women could work.

Generally, women tend towards monogamy – I have had a number of offers to become another woman’s mistress simply because she does not want me seeing other women. Men are far more laissez faire, prepared to accept the idea of compartmentalization because that is how they think themselves.

So if I did fall in love with a girl, and I have very nearly several times, I suspect I will hang up my Louboutins and leave escorting behind. Which I will miss.

Elise

A month at a time

An escort friend of ours suggested we get in touch with a friend of hers. “Elise has a totally sweet deal” she told us giving us Elise’s contact details. So we phoned. And emailed. And Skyped. And then we gave up because the one thing escorts are supposed to be is easy to contact.

Two weeks later we got a very sweet email from Elise. “I am so sorry not to have been available when you were trying to contact me. Let’s chat and I will tell you why.”

Always game for a challenge we emailed back and set up a time. An elusive escort is interesting.

Elise duly appeared on Skype and, to be honest, she was one of the prettiest, most vivacious, escorts we’ve ever interviewed. Lovely brunette hair in loose curls frames a wonderfully angular face and the sort of pale blue eyes people from Sweden or Iceland have. She was, so far as we could see, dressed casually in a perfectly ironed white cotton shirt. Again, it was a little tough to tell on Skype, although her lighting was clever, but we were pretty sure her shirt was well darted to ensure that her pretty breasts were accentuated without being flaunted.

Elise had a nice, well modulated, speaking voice and when she said “Well, as they say on Reddit, ask me anything.” we did.

First off, why so hard to reach.

“It is actually pretty simple, I only escort a couple of months a year. The rest of the time I am either travelling or working as a consultant or both.” said Elise as if taking a couple of escorting breaks in an otherwise busy schedule was the most normal thing in the world.

“I work as a revenue enhancement consultant for a number of world class hotels. I go to a particular property, spend a couple of months as a reception desk clerk or fill-in night manager and then write up what I see and recommend where improvements can be made. It is a bit like being a secret shopper but way better paid. The fact is that I can usually improve a hotel’s performance by a couple of percent which does not sound like much but really adds up in a three or four hundred room property.”

At the same time I love the cash I make escorting for a couple of months a year. So I arrange my consulting in three month pieces and leave a month between each one. That’s when I put up my red light as Sting would put it.

Escorting for me is a pure cash business. I have non-bank safety deposit boxes in a couple of US cities and I really do have one of those super secret Swiss bank accounts. If you know what you are doing you can set up a system where you can automatically route any credit card payments to Switzerland and you can arrange wire transfers as well. Especially if you have a few months in between the high cash escorting months.

How did I get into escorting? Well, before I was a revenue consultant I worked front desk at one of the best hotels in the city I grew up in. I was going to college and I could do that job a couple of nights a week. I didn’t need much sleep when I was a kid.

When you work front desk in a hotel you meet a lot of people. I worked during the week and most of the guests in our hotel were businessmen. Of course there were business women too, but say 80% of our guests were in town for a few days to get a deal done or a lawsuit settled. Our rooms were not cheap so we didn’t get a lot of salesmen or guys on training courses. Just a steady stream of executives, lawyers, accountants and the occasional owner – those guys took the best suites.

Front desk has a security function in a hotel. We are required to keep an eye on our guests but, more importantly, on people who are not our guests. Our guests take clients and friends up to their rooms all the time. No big deal. What we are watching out for are people who don’t belong. If we spot them we alert security and leave it there.

As long as there have been hotels there have been escorts going up to guest’s rooms. As long as the girls were discreet and nicely dressed no one blinks an eye. For all we know these girls are business acquaintances or friends and you don’t want to embarrass yourself or the hotel by suggesting that a girl is an escort. Plus, realistically, it is none of the hotel’s business if one of its guests wants some female companionship.

It is the hotel’s business if some gal comes wandering into the lobby with a skirt up to there and down to here, hooker boots and an attitude. Not because she is an escort, rather because she is a security risk. If you are a blatant hooker you are not going to get by the front desk unaccompanied, who knows where you will go in the hotel.

But I did notice that there were a few girls who I would see regularly. Nicely dressed. Usually with expensive shoes and sometimes with a really nice designer bag. Sometimes they would accompany a guest to his room, other times they would stop by the desk and ask for Mr. Smith on the house phone – which I learned was an excellent way to do a final check on a client. But the one thing they all had in common was that they were terrifically discreet. Yes they were glossy or a bit more glamourous than our run of the mill female guest, but they made sure they were perfectly put together.

We used to play a game on slow nights. “Escort or not”. A girl would go up to one of our guest’s rooms. How quickly would she return? If it was more than an hour but less than three, we said “Escort”. Not for any great reason, but that’s how we played.

One night, after an early shift, I went over to our very ritzy bar for a drink and saw one of “the girls” on her own. She nodded to me and smiled so I went over and joined her.

“I see you come in quite often.” I said pretty neutrally I thought.

“Nature of the business. I love this hotel. It’s always so clean.” she replied.

“And your business is?” I asked. Why not? I could always get up and leave.

“What do you think?” she said with a smile, “I entertain many of your gentlemen guests of an evening.”

On that basis we had a chat and, I have to admit, I was amazed. “Lucy”, not her real name of course, worked a day job full time and was entertaining in the evenings for spare cash. But what a lot of spare cash.

“1000 dollars plus tip. But I don’t watch the time. Sometimes I am there for twenty minutes, sometimes two hours; it works out in the end.”

Four nights a week, no more than two dates a night, usually just one. I am good at math but you didn’t need to be, Lucy was making $5000 a week minimum. Little wonder she was carrying a $3000 Prada bag and wearing Jimmy Choos. I was making, net, about $600 a week and was barely scraping by.

Lucy saw her date and excused herself. I went back to my white wine spritzer and began to run the numbers. In a month Lucy would make $20,000. Did she pay tax? Who knew and no one would if she was even a little clever about it.

This was huge for me. My hotel career was going just fine but it would be two years before I got a decent management job which paid more than a pittance. Plus, I had had an idea for the consulting business I now run. The fact was I could see where our hotel was missing revenue and I was pretty sure other hotels would run into the same problems. My idea of “embedding” in the front desk staff at various hotels made a lot of sense and I knew my own manager would be supportive if I went out on my own. The problem was how would I get by while I set up my business and hunted down customers. Lucy gave me a hint.

I had never really considered escorting. I mean I knew, or at least thought I knew what those girls were doing up in our rooms with their clients. But that is not the same as actually doing it. I got to work researching the heck out of the escorting business. Thank you internet. There was an awful lot to learn. Everything from escort advertising through to how best to screen clients to how to manage an escorting date. But there were also terrific online resources for escorts.

The good news for my potentially budding career as an escort was that I have never been at all squeamish about sex. In fact, even before I was an escort I enjoyed sex a lot. And it turns out that the way I enjoy sex, lots of enthusiasm and a fair bit of my being in charge, is a great way to do those consenting adult activities which are at the heart of every escorting date. But there is a lot more to escorting than sex once you start looking at it.

One thing I realized right at the beginning was I wanted to keep my escorting life completely separate from the rest of my life. Which was a bit of a puzzle because I wanted to do outcalls to hotels and, working in the business, I knew that it would only be a matter of time before word got around about my escorting activities. Oddly enough, the solution to the problem arrived when I had to go to a different city, not too far away, for a week long training program. Basically I realized I was an hour by car away from a completely different world. In fact less than that because I actually lived about twenty minutes away from my own downtown right along the freeway towards the other city.

Problem solved. While I was on the training course I arranged a cell phone in the city I was going to work in. And I took a look at some of the better hotels where I thought I would meet my clients. I scouted the various escort advertising sites and made some decisions about how I was going to present myself.

While I was doing this “legwork” I also was trying to figure out how I could best open my consulting business while escorting. Which led to my second “Ah ha” moment. I realized that it would be too frantic to try and escort at the same time as I was doing what I needed to do to build up revenue for a hotel. So I wouldn’t. What I decided to do is escort for a month, then do a consulting contract, then do another month escorting. My contracts were planned to take roughly two months and I had two lined up if I decided to take the plunge.

I gave my notice at my hotel and my manager, who had actually referred my first consulting client, was great and said I was welcome back any time. It was nice to know. The day after I gave my notice I put up my first escorting ad.

Anyone who says that escorting is an easy business is kidding you. Like every other business there is a steep learning curve. My first mistake – of many – was to assume that if I put up an ad I would suddenly have escorting clients. My phone was so silent I tried calling myself just to make sure it was working. It was. The fact was my ad was not getting the response I needed. Why not?

As much as anything it was because I was much too vague. I was all about “dining companion” and “pampering” which was fine as far as it went; but I was naïve enough to think that, along with a slightly sexy picture, would be enough. So I worked on my ad copy and did another, much sexier picture. I got a couple of responses but they were really time wasters who wanted a bargain. It took a while for me to realize that I had to really make clear that I was catering to executives who wanted more than just the “GFE”. Eventually, a week later, I got my first serious response. He was staying in a great hotel and he checked out on my screening.

I put on pretty lingerie, stockings, a great skirt and a semi-sheer white silk blouse. My hair was nice, nails done, make up right for evening and condoms in my cute little clutch. I hoped in my car and drove off to meet my first escorting client. Forty five minutes down the expressway and right into hotel parking. I’d arranged to meet him in the very pleasant hotel bar and I was there right on time. I secured a nice, out of the way, table, sat down and waited. And waited. And waited. An hour later my phone chirped out a text. He was stuck in a meeting and would have to reschedule. Not how this was supposed to go at all, but live and learn.

He was my first, but sadly not last, no show. From then on I didn’t get on the road without a confirming text of email. Happily, a day later, at a different hotel, I had a really delightful, and very lucrative, encounter with a very nice lawyer in his early sixties. I was a bit awkward and, as I was fumbling with a zipper in a pretty unseductive way, I blurted out that this was actually my first date. Things went much better after that and I was soon on my knees with my head bobbing up and down on a surprisingly big cock. No chance to take all that in my throat. But he enjoyed flipping me on my tummy on the bed, lifting up my skirt, pulling down my panties and, with a couple of shapish slaps on my bum by way of foreplay pushing nine plus thick inches of wet, hard cock right up my pussy. I was so glad I had put a lot of lubricant into my poor pussy before I took her out and sold her. He was a terrifically selfish lover and didn’t even think of reaching around for my pleasure. Instead he just kept pounding my pussy with his pile driver of a cock. After about five minutes, which felt like an hour, I felt the pace pick up and, with a manly grunt he was done. He pulled out and I just lay there for a minute or two. He went and sat in the chair where I had sucked him off and watched me.  I reached down and pulled up my panties and pushed down the back of my skirt.

“So that’s escorting.” I said when I had caught my breath.

“Pretty much.” he said his big, uncut, cock lying flaccid on his thigh. “Next time I will take some Viagra and have you a couple of times. Get you nice and stretched out.”

Next time, I thought to myself. Right. “Next time” is a good thing in this business.

He was delighted to be my first client and tipped very generously. He also booked me for the following week. A regular I thought to myself as I drove down the nearly empty expressway home.

That first month I had nine dates after a slow start. Not a lot but more than enough to keep me solvent as I got ready to do my first consulting gig. My idea of escorting a month at a time took a bit of a hit when my lawyer friend called the second week of the next month. Fortunately my first consulting gig was in a suburb of my city so I was not really “on the road”. I made an instant, executive, decision that if they called direct and I could I would see regulars even when I was not officially escorting. Which was, I think, the right decision. Besides, I was getting used to bending over and taking lawyer guy’s big cock good and hard. In fact I really liked it. The same every time, suck, flip, slap, pound. I didn’t want to miss that or the money. What I did do during my months off was stop advertising.

I have been working this system for escorting for nearly four years and, honestly, I can’t imagine not escorting. I could because my consulting business is doing very well; but, realistically, even though I charge a lot for my services as a consultant, the money from escorting is just too good to give up. Plus, and this only occurred to me after I had been escorting for a year, there was no reason I couldn’t combine my escorting months with living in different cities. I was already doing the travel thing with my consulting business and AirBnB knew my credit card off by heart. So, once a year, in the winter, I advertise in places like Tampa or Phoenix or Miami where I can get some sun.

Martine

Playing the Part

Escorts are often asked by their clients to do a bit of role play. Whether it is the naughty cheerleader or the police woman who will not take no for an answer, escorts can often make excellent money simply by gratifying the slightly unusual desires of their clients.

However, we wondered if there were not escorts who went a bit beyond the sex shop costumes and really took seriously the fantasy requests of their clients. While there were dozens of girls who offered “role play” along with the GFE and the pleasures of pampering, we had to really look to find a girl who took escorting role play to the next level.

We reached out to Martine on the basis of a really rather clever ad.

“I create worlds.” read the headline.

You have a dream. Detailed. Like a photograph and in it there is you and a girl or a woman or maybe several. You think it is a fantasy because you don’t think it can happen.

It can. I will make your dream real.

Immersive experiences take time to create. I have time. And talent and a deliciously perverse imagination.

Let us begin to make your dream come true.”

We reached out to Martine and soon had her booked for a Skype interview. From her name we thought she might be French and we were right.

“From Lyon. Which is a beautiful city but very, well, boring. So I went and studied theatre in Paris for three years.” Martine has a slight French accent and pronounces her English with an English rather than American accent. Very dark long brunette hair, bright blue eyes and shiny white teeth she is leaning in to her computer as she speaks. “Then I got an English boyfriend and moved to Brighton and studied more theatre but this time on the production side: stage decoration, lighting, props, make-up while I learned how English is actually spoken. We learn English in France but that’s not the same. I met a guy there who makes movies, little movies in New York and I went there with him. And then he left and I thought I could make some money without having an immigration hassle by escorting. And I did and that was ok.

The thing about escorting in New York is that the competition is crazy. All these beautiful girls. I was lucky because being French and speaking French is very valuable in an international city like New York. Plus I spoke a bit of German and a bit of Italian. Just schoolgirl level but that was way more than most girls could.

But I am not model gorgeous and I have average sized boobs which I won’t get done and I like being a brunette. I have blonde wigs and corsets and falsies and pushup bras. Plus you would be amazed what you can do with a little bit of contour stick. But I get ahead of myself.

I have always been attracted to the Southern United States. Probably because I loved “Midnight in the Garden of Good and Evil” when I read it as a girl. But also because it seems more European somehow. I just liked the idea of Charleston South Carolina. So, with a few thousand dollars which I had saved I loaded up my little Subaru Outback with clothes and makeup and nothing else and drove to Charleston. I didn’t know anyone. But I wasn’t worried. I had a bit of a plan. Very special escorting.

For my plan I needed a place where I could rent something quite big, a bit old and with lots of rooms. Obviously the touristy areas of Charleston were well beyond my budget. But what I was looking for was space and a bit of atmosphere.  It took a while to find the right place.

My idea was to create fully realized dramas for men who had particular fetishes, interests and peccadillos. Most men do, at a very limited level; but some men have elaborately worked out ideas about what they would really like. Escorting in New York I would say one in five or six of my dates were interested in something which went well beyond the world of the dungeon dominas or dress up games we read about. And some of these were men had a good deal of money. In New York my escorting fees were high but the agency took so much.

I thought there might be a market for an escort who was, essentially, a destination provider. It was a bit of a risk but I realized that with a clever website I could reach out to, literally, the world. Were there men who could afford the costs of a fully realized drama in which they actually lived out their sexual fantasy. Not a pale imitation, rather a carefully crafted, well staged realization of the idée fixe they had carried with them since they were fourteen.  If I built it, would they come?

Just the right place turned out to be a large apartment and what had been a storage loft above a store just outside the historical district of Charleston on a little narrow street. It was a mess. Cobwebs, dust from the Civil War, lots of mice and their leavings. I couldn’t live in it, much less escort from it, for nearly two weeks while I cleaned and had two nice young men paint each of the rooms a lovely, light grey with gloss white for the trim. The storage loft remained unpainted. It was to be the stage. When I was too tired to clean I worked on my website and began to compose my ads. The good news was that the place was very inexpensive and, under the layers of dirt, really rather charming.

I did not advertise my special escorting service in Charleston. I knew I could make a good living escorting locally but I actually wanted to create a different sort of experience and my sense was that to be a local escort would get me involved in a world I preferred to stay away from. Plus, and this was a big consideration, I wanted to be entirely invisible to local law enforcement. I was still not quite a legal resident of the United States.

So, in my advertising I don’t mention my location. Which, no doubt, costs me more than a few escorting dates but, well, c’est le vie. If a gentleman gets in touch with me and passes my screening, which I am very strict about, I first tell him my prices and, if he does not blink, I give him my location. Charleston is actually quite close to a lot of big cities in the US. Two hours from New York, a little more from Chicago, a little less from Miami. And my clients are all frequent fliers.

Men looking to have the dream of a lifetime made real don’t blink at a couple of hours travel. Nor do they blink when I send them the costs of building out the scene (or scenes) for their fantasy. As I say to prospective clients, “It is all smoke and mirrors but done well that is all you need.”

Over the time I was an escort in New York I read a lot about the exotic inner sexual lives of men. I also asked my clients a lot of questions. It is surprising what a man will tell a girl who has just given him a wonderful time and whose company he wants to enjoy a little longer.

Men obsess about many things and some of those things are impossible to really access; but for things like watching a girl in a bathtub through a window or being trapped in the changing room of a lingerie shop or having Auntie giving her naughty nephew a good spanking and sending him to her room? Well for all of those and many more there is the gentle suspension of disbelief which is the essence of theatre.

My escort dates are a minimum of a single afternoon or evening, although I prefer two. And I absolutely require two full week’s notice and a deposit which covers the costs of the set and whatever I am to be wearing, carrying and so on.

The reason I prefer two encounters is that I like to spend time during the first (almost always non-sexual) encounter, going over the requirements and the script. Escorts on regular dates are often asked to say things or do things by their clients. Within the context of a two hour date there is no lead time between the “ask” and the escort’s getting to business. I think that is not nearly as erotically satisfactory as moving from a conversation on the first night to a fully scripted scenario on the second. I am very good at memorizing my lines and, with an hour or two’s practice, I can deliver them just the way my client needs me to.

There is a very lovely hotel a few blocks from my apartment which I encourage my clients to book in. It has a very European feel and, at the same time, a wonderful Southern sense of hospitality. I know the manager as I often, when I am not working, will have a late breakfast in their airy, terraced, dining room. I do not, however, dine there with my escorting clients. Rather I meet them in the hotel bar, portfolio case in hand.

Charleston is one of the few places I have been to in America where a woman can dress nicely without attracting unwelcome male attention. My lovely grey, pink silk lined, pencil skirts, heels, hose and crisp white shirt will certainly gather their share of glances, but I can walk into the bar secure in the knowledge that only my gentleman will come to my table.

Our first meeting is about business and about story telling. Of course payment details are concluded; but the real business is my client becoming comfortable enough with me to give me the details which are vital if my performance is to be convincing. For this conversation I like to go to a charming restaurant, have a little wine, perhaps let a button or two on my blouse fall open but, most of all, put my client at ease. It is a luxury most escorts really can’t afford simply because time is very much money. For me, though, I make my arrangements prix fixe. I am paid a flat, very generous rate, for the time I will spend with my client.

In the course of our conversation we cover, lightly and hypothetically, what triggers and keywords my client will enjoy the following day or evening. Minor details of my dress and demeanor can be discussed playfully over dinner. Of course we have more than a little wine and by dessert my client will often be telling me what he really wants from this theatrical escort encounter. Men are surprisingly specific: patent leather stilettoes not matte leather. A chaise rather than a bed.

Part of my service is to get all these details right. If one of my escorting clients wants an encounter with a maid I will find out as much as I can about her uniform, her hair style, where the encounter should occur. It is a lot of preparation but, as many of my clients return again and again, apparently the effort is worth it.

The one thing I am meticulous about is getting the period right. My clients’ dreams, their fantasies, are almost always very tightly locked into a particular era. They may not even realize it. When I am speaking to them when I book the encounter I try to get an idea of the relevant dates; but it really is over dinner that I narrow it down. That encounter with the sultry older woman? It happened on a specific day in a specific month of a specific year. What would the background music have been? Would she have smoked? What sort of bra and panties would she have worn? Girdle? Permed hair? If she wore a dress what was it likely to have been made of.

I don’t offer the standard escort encounter. I offer the Remembrance of Things Past, the Proustian madeleine which lets loose a torrent of memory.

When we have finished dinner I walk my client back to his hotel, bid him à bientôt and give him my address and the time he is to be there. Then I go home, jot down notes of our conversation and go to bed. I know I will have a busy day. Armed with my notes I find the finishing touches to complete the illusion. Knowing a few vintage clothing stores, a few nice antique stores and having a growing collection of mid-century knick-knacks I can usually “dress the set” and the escort to my client’s taste.

Most of the time I am conjuring scenes from my client’s youth. But sometimes it is more complicated and my client will want a scene in a fin de siè·cle French brothel or he’ll want to “breed” a corn fed Iowa blonde farm girl in a barn pulling down her jeans and her white nylon panties over a bale of hay. My job is to get all that right. (Hay is scratchy, have a horse blanket handy.)

I have a couple of girls I work with when I need extras. They are escorts and they are paid very well for doing, frankly, very little but looking decorative in whatever I tell them to wear. Sometimes they are there as “extras”, sometimes they are involved in the scenario. And sometimes a client will simply want an audience for whatever performance we are undertaking.

Most of my escorting clients have been nursing their dreams for years. Sometimes for decades. They have tried to find escorts to accommodate their desires but, while these girls have tried, they usually fail because they are not specialists. They don’t have the time to find a 1950’s waitress uniform much less figure out how to embroider “Agnes” just above the left breast. I, on the other hand, have a sewing machine with an embroidery function.

As I have said, my client’s desires are usually incredibly detailed once you scratch the surface. You can’t get all the details right but if you manage to hit 70% on the first encounter you will have a very happy client. And, like every successful escort I have ever known, I have wonderful regulars.

I am very upfront about the fact I want to improve my clients second and third encounters. If they agree they will be coming back, I will spend time on email and the phone, walking through our first encounter and taking their notes as to what was right and what needs work. We collaborate and we improvise and, usually, by about our third special escorting date we will be closer to 93% right.

When we have reached that point where everything is redolent of the period and the sensibility they are looking for, I often suggest variations on their theme. By this point they see me more as a friend than an escort and they see the money they are spending, which is substantial, as an investment in a series of encounters in which they are transported to a world entirely outside their day to day life. Apparently this is addictive.

As you might guess I cannot do too many of these escort performances in a month. Even with regulars where I have all the furniture, music, fragrance (a key component, thank you eBay) and lingerie, I still have to construct the set and work out the script.

Of course, given what I charge to do all of this I don’t need many escorting encounters to live very well indeed. Charleston is a lot cheaper than New York or Paris. And, quite honestly, a pretty young French woman is never lacking in company and invitations. I have discretely let it be known that I have a private income, which, in a way, I do.

Because I do not escort clients from Charleston and because I like to dress elegantly but demurely, and my little private theatre is unknown to the people I am meeting, I have, rather carefully, admitted that I get financial advice from time to time which explains any situations where I am seen with a rather older man. But, even if some of the smarter ladies have an inkling, as I make a point of not flirting with their husbands I find doors open to me.

I have a slight dilemma with taxes but I resolved that by creating a small Canadian consulting company which declares its US income. Because it is a company the question of my immigration status does not come up as a result of my paying my US tax. I have a federal tax number. That is enough I think.

I’ve been doing my special sort of escorting for nearly three years and now, having raised my rates twice, make more than enough money to live very easily in Charleston. I can get anything I want or need online or in the clever little stores in the city. Plus and this is a huge bonus for my business, there is a wonderful tradition of tag sales and estate sales where fabulous vintage things are practically given away. Plus there is the Junior League. Mon Dieu, lovely clothes practically given away.

There is no reason at all why I will not be doing my little, private, theatre for years. Unlike the really competitive world of regular escorting, I have a small, select group of clients who, honestly, don’t really care if I am young or conventionally beautiful. They care that I can evoke the memories they have carried for decades.

Because there is, usually, activities between consenting adults I have no doubt that I am escorting. But when I am up late sewing the fourth petti coat for a naughty French teacher’s 1955 faux Dior dress, it feels much more like a piece of performance art with, perhaps, a happy ending. For sure it is escorting but it is also work that I love and am very good at.

Jasmine | Bree | Candace | Rosy

Escort Style

I can make a pretty good argument that style is a hundred, maybe a thousand, things and every girl evolves her own. But the one thing which you can change is actually being conscious of your style and the style to which you would like to be accustomed. For an escort style is not an optional extra. In fact and escort’s style often determines how often she is booked and what her rates can be.

Having a personal, signature, style lets you make a lot of choices easily. Knowing how you are going to present yourself makes dressing for an escort date simple, quick and painless. It also makes it easy to shop for pieces which will work with the other pieces you have which define your style.

But what is an escort style?

Obviously there is a huge variety when it comes to escort style and we’re not going to cover all of them in a short article; but there are a few themes which have run through conversations we have had with escorts.

Ladylike

“I always dress like a lady.” said “Jasmine” who has been escorting for three years in New Orleans. “Down in the South that still means a skirt or dress, stockings after Labor Day. But of course, when you are escorting you want to add a little spice. But not too much because I often see gentlemen in hotels and, even though this is the Big Easy if you look too hot you are going to get hassles at the front desk.”

“I do a couple of things just a little differently. For example, while I hate stripper heels and won’t wear them, there is nothing wrong with an elegant pair of heels. Steve Madden makes some gorgeous, wearable sandals and pumps with a surprisingly comfortable four inch heel. I wait for the sales at Amazon and buy a couple of pairs. They look wonderful with a skirt or a little shift dress. They are just a little higher than I would wear in my regular life but that inch makes a huge difference.”

“The other thing I do is try to dress in layers. A little jacket over a low cut sleeveless dress converts provocative into promising. Ideal for hotel lounges when you are meeting a client.”

“Most of all, I try to make sure everything I wear on an escort date, from panties on out, is very, very feminine. These days men work with women who have adopted a sort of androgynous, anti-sexy look. I understand that but the reason my escorting clients come to see me is to get away from that world. At work or at the mall or at their kids’ activities they almost never see a woman in a skirt much less a dress. For the time they are with me they are going to be able to enjoy the little bits of lace and clever tailoring  they can’t get at home.”

“I don’t know if all my clients really notice the effort I make to be feminine; but I do know that I have a couple of dozen regulars and they all compliment me on what I am wearing. Plus, and this is actually more important than I thought it would be, rolling on stockings, pulling a slip over my head, picking out a dress, shoes and a bag, takes me out of my day to day life and puts me into the mood for escorting. Sure, I could do the job in a track suit but I don’t think I would do it for long.”

Cali Girl

A completely different tack is taken by “Bree” a twenty something escort who works in a small city on the California coast.

“I do have a style. Of course I do. But it is pretty much my personal style as well. I don’t have that big a gap between real life and escorting. I mean I got into escorting when a guy at the bar I waitress at made me an offer. He didn’t want me all dressed up, he liked what I was wearing to serve drinks.

So my “style” for escorting and for the rest of my life is really not all that much about clothes. It’s all about the body, the hair, the make-up, the skin: start here. I am a gym rat. I work out pretty hard three days a week – cardio and light weights. I have a trainer who checks me once a week.  At the rec center I work out at there is a pool and I swim three miles a week. Just lengths, not super-fast.  I don’t own a car but I have a bike and the city I live in is super bike friendly so I ride pretty much everywhere.

When I was 18 I had my boobs done. Not huge or anything but a nice full D cup. I have a narrow back and a tiny waist so I cause a bit of a stir when I wear anything which is even a little tight or revealing. and, obviously, I am toned so I can get away with a lot of pretty revealing clothes if I want to. But, being toned is not nearly enough if you want to make really good money escorting. You have to work on your skin a lot.

The guys I see watch a lot of porn and they have really high standards for the girls they are willing to pay. They don’t want little bone rack models and they don’t want girls who, when they take their clothes off, are all pasty. I’m pretty lucky because my apartment has a really private balcony where I can tan naked. Not too much, just enough to soften the bikini tan lines. And I know this sounds weird, but even when I am tanning I actually wear sunscreen. I want my skin sun kissed not tanned.

“Part of my style, I guess, is that I wear really lacy, really white lingerie. White thong panties and matching, really dazzlingly white bras. I pay a lot for my lingerie. Or I used to, now I have a guy who loves taking me to a couple of the better lingerie boutiques in town and buying me the really nice French and Italian brands I would never be able to afford myself. It is a perk of the escorting business to always be wearing La Perla or Aubade or Cosabella lingerie. And, of course, the reason I always wear white is for the contrast with my lightly tanned skin. In the right light it is pretty dazzling.

The one other thing I do for body care is a full mud bath, exfoliation, facial and deep massage every week. It costs a bomb but it’s totally worth it. I have a regular session on Thursday mornings. Plus manicure and pedicure and any waxing, ouch, which is needed.

I have naturally blonde hair which, I admit, I use a bit of lemon juice on to streak. I keep it in a long bob but I am obsessive about having the ends trimmed twice a month. I like to look like a very up market beach girl.

On dates I do wear heels. At least the first time. I have a nice pair of vintage platform mules with a five inch heel. Why, yes, they do make my legs look longer. I am already five foot six so these make me five eleven. Clothes are pretty simple. I like little cotton skater skirts or body-con dresses. Sure, they are short but all the girls on the beach wear short skirts.

I keep my make-up minimal. A slick of baby pink lipstick and a little mascara and I am good to go. On a big date I might wear a bit of eye shadow but only if I want to. The thing is that for me make up makes me look older and older is not what my clients want. They want a young girl who seems eager to go down on them and just can’t wait to lift up her skirt and pull down her panties. They want to know I am legal but they want to pretend I’m not. Which is fine with me. I make a lot of money from old, rich, pervs.”

My clients are buying the fantasy that they somehow can pick up a girl like me. Escorting is all about the fantasy and in my heels, a pretty white skater skirt and a white tank top with the lacy straps of my bra as part of the outfit I am, honestly, quite a package. Most of my clients are pretty relaxed. They’ve made their money and they don’t actually care if they are seen in public with a hot girl who looks like she could be their daughter. I mean what’s the point of having a $200,000 convertible if you don’t have the big boobed blonde to go in the passenger seat. I mean I like have entire dates where the big deal is driving. I suppose you could call them “car dates” and I have been known to reach across the transmission.

So, my escorting style is all about fresh, young. Sort of a cross between Katie Perry and Taylor Swift. Middle aged men love Taylor Swift. I think I’ll be able to pull it off for a few more years if I take really good care of my body. And that’s all I want anyway. You can’t live on the beach all your life.

Working Girl

I’ve been escorting on and off since I was twenty.” said Candace who is now in her early thirties. “When I was younger it really didn’t matter what I wore or how I made myself up or whether my hair was done. Guys love young escorts, period. But now I am older and a lot smarter. A lot smarter. I want to work half as hard and earn twice as much.

I live in a North Eastern city. I won’t say which one but I will say that it isn’t New York. I wish it was because I love New York. I try to get to New York once every couple of months and I have a few escorting clients there who make it worthwhile.

I am pretty tall, five ten and I try to stay fit. When I was in my twenties I started highlighting my hair.  The blonder I went the more I seemed to make as an escort, so now I am essentially a dirty blonde. I keep my hair fairly long and ten minutes with curlers and a blow dryer and I get a nice wave.

I have a particular look which I developed watching women who seemed to have the life I want. These are not girls, they are in their late twenties and early thirties. I don’t know that they do during the day but, after five you see them in the nicer lounges, restaurants, at concerts and at gallery openings. They have this really clever style which somehow suggests they have arrived. That they don’t need to “try” any more. That the look is just effortless.

I can tell you it isn’t effortless. First off, one of the reasons these women look so good is that they buy designer inspired clothes. I say “inspired” because, if you look closely, they are often not actually wearing a designer dress or they are but it is four or five seasons old. But they look so expensive, so glossy, so unattainable.

For me, escorting is a means to an end. Always. When I was a kid escorting was a way of having a bit of extra money while I went to college. Now it gives me the free time I crave. I really should have been born with a trust fund but, well, I wasn’t. I like to go deep on my own projects. I have a couple of businesses, one online, one in the real world and they take up most of my days. Being in business, even though both businesses are essentially creative, also influences my style.

I have developed a look which lets me transition from a set of business meetings in the morning to a naughty escort lunch in the afternoon to a cocktail date after work. Of course I “don’t look like an escort” whatever that means. Seriously, no girl I know who is working above street level does the boots and booty shorts thing. The clients hate that look.

Creating that style was all about dual function. First off, my business outfits are all a bit edgier than what most women wear to the office. Never pants. Always skirts. Usually suits and often vintage suits. The great thing about a suit is that you wear a sweater – which if you tuck it in can show off your assets – or a shirt which can stay buttoned up in the office but is easy to adjust for an escort date. I also make sure that I have my nails nicely trimmed and painted and my make-up just so.

When I am escorting I like to have a more dramatic make-up but I start the day with a really simple primer, foundation and simple eye shadow, mascara, a pale lip and that’s it. Now, five minutes in front of a mirror and with some contour and a bit of eye liner I have a much bolder look. Swap out the pale lipstick for something really red and I look very grown up indeed.

My look, my style is entirely geared towards the older, more sophisticated clients I cater to. They want to spend their time with a pretty girl who, almost by the way, happens to be an escort. That’s what my style delivers.

The Girl Next Door

I don’t know if I really have a “style.” said Rosy who is a twenty three year old escort working outside Chicago. "I mean I do have outfits I wear on escort dates but they are pretty much what I wear everyday as well. All my advertising is about “The Girl Next Door” so that is what I try to look like. Which really isn’t a stretch.

I don’t really do glamour. I have a couple of nice dresses but I feel sort of awkward wearing them on escort dates. They really are not me if you know what I mean. In fact I almost never wear dresses of any sort, nice or not.  Girls my age really don’t.

I mean I am twenty three. I do a few courses at the community college near where I live. I do the escorting pretty much to have a little money for extras. I have a job too.

The thing is I just sort of fell into escorting a couple of years ago when I really needed to make some money and a guy offered me some money to go with him. I went, he paid and here I am. My escort dates are almost all in calls at my apartment. So it is a lot easier for me to be sort of natural. You know, wear what I am wearing anyway.

The only thing I have really changed is that I wear front closing bras. The reason I got into this business is that guys are always staring at my chest. I’m pretty big and my boobs are the only part of me that is. The rest of me is what they call a spinner’s body. Because I work out and do yoga.”

So really, my normal escorting outfit is a pair of high heels, a little skirt with a shirt or sweater – always with buttons because guys love the reveal – and that’s it.

I keep my make-up really light. If I put on foundation I look about thirty and that is not a look which brings in the clients. So just a little blush, mascara, a tiny bit of eye shadow and a bit of eye liner and I am done. I wear a pale pink lip gloss because it doesn’t show on client’s clothes. Which is important because like practically all my clients are married or with someone.

The one thing which is, I guess, part of my style is how I have my apartment. It is really girly. My bedroom is pink and I have this really cute canopied bed. I have a pretty little white vanity. In my living room I have some chairs which I slip covered and put some ribbon on the back. And this great white shag carpet and sheet, billowy drapes.

A lot of my clients are regulars and they bring me little gifts which go with my décor. I somehow have started collecting little china dogs and I have one regular who brings me a couple on every visit.

There is a lot of fear some guys bring with them when they see an escort. They’ve heard stories of girls trying to rob them or being on drugs. As soon as I open my apartment door they know they are going to be safe. A lot of that is about having a nice light apartment which I keep really tidy. I know that really isn’t a style thing but it is something a lot of my clients comment on.

Most of my escorting clients are a bit younger. Guys in their thirties, usually married, child seats in the back of the mini-van. They want fun and no drama and seeing a cute girl in a short skirt with an extra button undone come to the door re-assures them. If I have any style at all it is all about not being intimidating. My outfit, my make-up, my hair and my apartment all say “Welcome, relax, let’s have some fun.” And we do.

Being the “Girl Next Door” takes my clients back to when they were in high school.  The difference is that now they know, because I’m an escort, they can be pretty sure the “Girl Next Door” is going to “go all the way”. They like that.

Charlie

Private Dancer: A stripper and an escort

“Stripping is a funny business.” said Charlie a twenty four year old blonde who we reached in Texas. “There are all sorts of rules. Every municipality can have different rules about full nudity, partial, none. Then there are lap dances, if they are allowed at all. And every club will have its own official rules and then there are the unofficial rules. It can all get pretty complicated if you’re like me and travel a bit.”

And then there are the patrons. When I first started stripping I was pretty intimidated by dancing in front of anywhere from a dozen to a couple of hundred men. After a while I realized that most of the guys were there for a good time and a few hours away from their jobs, wife, kids. They were pretty normal.”

Sure, there are always assholes. But that is true in any job.” said Charlie, “if there is a problem with stripping it’s the way some clubs rip off the dancers. Every club is a bit different and you need to know what is going on before you ever swing from the pole.

The clubs I like to work in pay a flat rate per shift or even, for feature performers, per dance set. Usually three or four songs. And you get to keep either all your tips or your tips less a tip out to the DJ. Others don’t pay you anything for the hours you are there: you just get tips. But the clubs I try to avoid actually charge you to work. Basically they have a house fee that you pay and you keep your tips.

When I first started stripping I had no idea how competitive it was in the clubs where you can make really decent money. Getting up on the stage and taking your clothes off is not at all how it works. First off you need costumes. Start with the heels. No girl in any of the clubs that are worth working in strips in any less than a four or five inch heel. You can buy cheap shoes but they kill your feet and they fall apart. A good pair of stripper heels will set you back minimum north of a hundred dollars and I have two pairs which cost me six hundred apiece.

A lot of the girls have custom made outfits with cute little tear away skirts and double bras so you can tease more than a little. If you are going bare you usually want a panty which has some sort of fastening at the hip.

After about two months in the business I had spent nearly $1000 on a couple of outfits but, I have to admit, they really were not me. I am not a rhinestone and sparkles kind of girl. And, the whole point of the outfits was to stand out and if you are surrounded by half a dozen pretty girls all wearing rhinestones and sparkles you don’t. Plus, I wanted to work myself up to being a featured girl.

The whole feature thing is a business in itself. Have you been in a magazine? Playboy? Big websites? Have you done porn? There are porn stars who make more stripping than they do from their movie work. They have a national audience and they will pull guys into the club. I’m not a porn star. It’s not something which appeals to me at all. But I was up for modelling.

And there is another hugely competitive business. Realistically, there are a lot of pretty girls out there and a lot of them are more than happy to be photographed naked. If you are just a straight nude model you don’t make much on most of the photoshoots. And you really need to be in New York or Los Angeles. But I got a few shoots. Most of it goes straight to the web. But you get the clips. Which you can put up on your own site.

I am lucky.  I was born with naturally quite large breasts and a tiny back and waist. I work out to stay really tight and it pays off. It doesn’t hurt that I’m a natural blonde either. I am quite pretty in a fairly innocent sort of a way. And I know my way around a make-up table. Pro-tip: lipstick and a little gloss on your nipples is fabulous, a bit of blush on your pussy lips…and a dab of glycerin to make you look a bit wet, golden. Literally, tips go up 50-75% is you look as if you are on heat.

What I realized going on photo shoots was that I needed a “gimmick”. Something which made me stand out. That’s when I invented Charlie. All the girls have “show” names. And they change them up from time to time. The thing is, if you want to become a feature girl you need to build a bit of a brand. If you aren’t doing porn, that brand has to be web driven. You put your magazine shots up on the web and you start doing a bit of social media. But it needs to focus on a name and people have to remember that name. You remember the old Johnny Cash song, “A Boy Named Sue”; well I thought that a stripper with a guy’s name could work. Plus, there was a perfume back in the what, seventies, called Charlie my mum used to wear. Anyway, I decided that I’d use that name and work at branding it.

Once I made that decision I also decided that I would try to come up with a “look” which was pretty distinctive but which didn’t cost a fortune. I love the whole burlesque vibe and the queen of modern burlesque is, undoubtedly, Dita von Teese. Now obviously Dita is working the whole dark brunette, scarlet lip, pale white skin thing and that is not going to work for me. But what she is also rocking is a whole retro lingerie and outfit sensibility.

If you want to stand out in a bunch of girls wearing rhinestone encrusted, man-made fiber costumes try wearing a 1940’s secretary tailored suit or a real, white cotton, nurse’s uniform with lingerie to match. It really was fun to do all these outfits which were totally unexpected. Plus, you can get the most amazing vintage stuff online.

I worked the retro lingerie into my sets first, but one club manager just loved the whole idea and he encouraged me to develop Charlie as a feature act. We figured out a bunch of music which could work – everything from hot jazz to Michael Buble with plenty of Frank Sinatra and Tony Bennett. As the manager said, I was single handedly reviving the glory days of strip tease.

It took a while but between my website, my twitter feed, Instagram and Facebook I was beginning to build up my brand. I always made sure the DJ mentioned my Twitter handle at the beginning and end of my set and I had business cards with my online stuff printed which I would give to guys who came to my shows.

I kept my shows fresh by actually having “characters” Charlie would become on stage. My nurse would take the temperature of some random guy on gynecology row – that’s the front row where the close up artists like to sit. I had a great old camera on a tripod which I used as a prop for a pretend pinup shoot. The thing was that all my costumes and my props had to fit in the trunk of my car so no “Ditaesque” champagne baths for me.

After a while the whole retro “Charlie” brand began to catch on and I’d get club managers booking me, through my website, in different cities and, eventually, different states. If the money was right I’d go. I mean I am not a headliner like the porn girls are, but I am a draw and that is really all the managers care about. Plus, I got a few more magazine shoots which increased my online presence a lot.

Adult entertainers get asked out a lot. Well, you get propositioned by guys with a few more drinks than was wise a lot, but there are a lot of high rollers who like the idea of taking a feature girl out for dinner and a good roll in the sheets. And they will pay very well for the privilege. When I started I never went out with patrons. But when I invented Charlie I decided that the money was too good to resist. One porngirl I knew was making big fees at the clubs and double that for one date a night.

You have to be very careful because a lot of clubs will ban a girl who is seeing gentlemen on the side. Which is why my website is so important. If a gentleman wants to see me and asks in a club I give him my business card and write a “members” code on it. I’ll say, “I never discuss dating in the club but I’ll be online tomorrow at 11 and you can use this code to get into my members area.

Truth to tell, only about one in five make contact which is fine with me because I hate to waste my time. The guys who don’t were never going to pay my fees.”

My members’ area is very discrete. It is all about private dancing with Rumbas going for one price and the all in Tango, for quite another. I have a contact form and it asks for the information I need to screen my potential client. I have a booking fee which is pre-payable by PayPal and is non-refundable. I don’t mind no shows but I make sure I am compensated for the time.

Because Charlie is such a retro girl on stage, I make sure she is off stage too. Which my private clients love. I always insist on dinner or a drink in what Charlie would call a “swanky establishment” before the private strip tease in a nice hotel. I have arrangements with a couple of really nice hotels in my home town and one or two on the road. A suite is so much nicer than a room and a girl with a living room can entertain gentlemen callers without any questions being asked.

The whole “Charlie” brand is about “every inch a lady” and I think my private clients really appreciate that. Yes, I may take my clothes off in public; but that does not change the fact I expect the very best. For a high roller the price of my time is the least of his worries. What he is looking for is something as different as I am on stage.

For my private dancer encounters I always make sure to keep the Charlie brand intact. No “stripper” heels, retro lingerie, stockings of course: if we are going somewhere nice for dinner I’ll wear one of my vintage evening dresses. Unless my client asks that we be discreet, then a 50’s wriggle dress and nice black heels will work. But most of the men who will take a stripper out for dinner want to be seen with a va-va-voom girl on their arm. I aim to please. I have the great dresses but also wonderful old fur pieces. There is really nothing sexier than a low cut dress with a white fur stole. And the fun part about fur is that, because it is not so terribly Green, you can get $5000 pieces for a few hundred dollars online or for $50 at estate sales.

When Charlie is onstage she sometimes wears a lot of glitzy but fake jewelry.  The patrons are not there to see jewelry but they seem to enjoy the sparkle of the lights on the necklaces and bracelets I have been able to find in vintage stores. But on my dates I like to wear real jewels. I can’t afford diamonds – though I got a very nice diamond bracelet as a tip, but you can get nice pearls for not do very much at estate auctions. The secret with pearls is to wear a lot of them. Those nice sorority girls can keep their single string of pearls, I like half a dozen of slightly different lengths. I also have a couple of jet pieces – that is a black stone – and some nice old black glass which can work with some outfits.

The whole point of a date with Charlie is that you are taking a performer out for the evening. I am happy to be introduced as a dancer. It really works for certain sorts of high rollers. They like my slightly over the top outfits, the fact I have any number of clever and very low cut bras with gravity defying capacities, the make-up and the false eyelashes. Dating a bombshell is not something many men do in real life. Charlie gives them the full bombshell experience straight out of the 50’s when nice girls didn’t.

One thing which I had not anticipated is that Charlie gets booked for things like stags and poker parties and football games. The first time I was asked was by a private client who had such a good time he wanted to share it with a few close friends. They have a friendly, but fairly high stakes poker game once a month and my client wanted to surprise his pals. I named a huge price and he gave me a cheque and an address.

You’ve heard of man caves? Well this house had a whole separate area which was set up like a garage but other than the three super expensive cars that glistened, it was just devoted to what this guy liked to do. Big pool table, giant wide screen TV with a couple of others around the room, a full, twenty foot long bar and what I would call a “card room”. It really did look like those places you see in some states where you can play cards any time of the day or night. Except those always look a bit seedy; this one had three tables, great lighting, a plush carpet and lot of room. Of course there was a fantastic sound system and I’d brought music on my phone. Behind the bar were two pretty topless girls who my client had mentioned were just there to serve drinks and snacks. I was the entertainer.

My client wanted me to do three short – he emphasized short – dance sets over the evening. That was it, He even set up a great dressing room for me with a vanity, makeup lights, a rack for my costumes, a chaise and my own little powder room with a shower.  I had the feeling I was not the first stripper to work his card parties.  At one end of the card room set up there was a raised platform and, yes, the ubiquitous pole. Charlie did her three sets – Nurse, old time burlesque queen and naughty librarian.

I was not surprised or offended by a few knocks on my dressing room door over the course of the evening. Very much expected really. However, even the big winners offering the biggest tips had to be contented with my enthusiastic oral attentions. Only the gentleman who hired me was going to be completely lucky that night. Didn’t seem to bother the card players and my version of a behind closed doors lap dance with a very happy ending suited them all just fine. I realized my rates were a little low when I saw that the ante was $500 a game at the beginning of the evening. Nothing wrong with a raise I thought to myself after my first show.

Doing a half dozen to a dozen blow jobs a night between sets as Charlie might be a bit wearing if I was doing the full meal deal. But in my dressing room I really just do a tongue bath and then slip the condom on, and start up a really good handjob while I talk to the man and look up at him. Telling a man what a fantastic cock he has and how much you would like him to fuck you but you can’t takes all of a couple of minutes and he’ll be ready to squirt. When I feel him getting close I say something like “Now shoot that load into my little mouth” and wrap my lips around the head of his cock. I never break eye contact. If he needs a little push I will reach up under his shirt and pinch a nipple or I will play with his back door with one of my long fingernails. Never fails…Next, please.

It turns out there are a lot of super deluxe man caves in the great state of Texas and Charlie has been invited to many of them. The big challenge was not repeating my costumes too often and getting the timing right with my stripping gigs and escorting dates. But, the money is fabulous and with a bit of organization I can usually make everything work.

What I have learned with Charlie is that being a little hard to get is a huge bonus at my level in the business. I try to work in the clubs a minimum of ten nights a month simply to keep Charlie’s name and brand out there. Three or four nights I will have a private dancer date. A couple of times a month I will do a private party.

I have had this schedule for Charlie for the last couple of years and it works really well. I am very close to my financial goals so now it’s a question of how much longer Charlie will want to be an adult entertainer. At a guess she’ll retire from the club stages first. That is very hard work for what you make compared to what you can make as a private dancer. But Charlie the bombshell date and man cave entertainer? I suspect she’ll be working for several more years. You can always have bigger financial goals.

If you enjoyed Money Sex I am sure you will like some of my other books about girls who make great money and lead elegant, fun, luxurious lives as top end escorts or being kept as wealthy men’s mistresses. Writing these books I think of my younger self making her way in the world…these books would have helped me avoid mistakes and make the most of the fleeting beauty of youth.

Pay to Play – Hannah Jay

Avails: Escorting for the Elegant Woman
http://amzn.to/2fMzPND

500+ pages of style, sex tips, business affairs, marketing, advertising and photography as well as how to do dominant dates, make fetishes fun, wear stockings, enjoy slips and corsets, wear towering heels and be every inch a lady. If you are thinking about escorting, are escorting or simply want to know more about the world of glossy, expensive, fabulous women who accept the cash compliments of the men they sleep with, this is the one book you need.

Questions for Miss Jay: An Escort's Guide to Style, Dates and Fun
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Questions from escorts – How much to charge? What about threesomes? How to be elegant as a man worships your feet? What about a client who wants to shoot a selfie…that kind of selfie. Self confidence, style, a whip in your designer tote a vibe for that toy show your client will pay extra for.

“Excellent, engaging and detailed guide for not only those looking to become "professionals" but also for those simply looking to improve their "feminine impact" with its savvy tips on upgrading personal style and presentation. Miss Jay is a refreshing voice for the new feminist age and her fun, playful outlook on courtesan life is both entertaining and liberating.” Amazon 5 star review

MODERN MISTRESS: LEAD THE LUXURY LIFE YOU DESERVE
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How to look glamorous and very expensive. Sex tips - enthusiasm, technique and a nice pair of stockings. The Modern Mistress's apartment, wardrobe, lingerie, sheets and refrigerator: a complete guide. Wealthy gentlemen are looking for pretty girls to pamper…why not you?

Money is the tribute age pays to beauty.” said a wise old roué. Many worldly women have been kept for a few years in their early twenties or thirties. They are the lucky ones with elegance and style beyond their years. They “know”…other women merely guess.

On the other hand, if you would like to read about my own, dominant wife lifestyle where my husband serves me and is kept in chastity, regularly sent to his corner to remember his place and caned weekly, well, here you go.

FemDom Marriage

A Man in My Position
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And we begin. Written by my submissive, chaste husband, this is the story of how we realized that a happy life needs a dominant wife. My sweet elliot is all alpha by day but he needs to be disciplined, denied, sleep in a nightie and learn to obey the only woman he has ever truly loved. Yes, I am afraid I do have to cane him and bath brush him… but he gets to pleasure me quite a lot and, very occasionally, I even let him slip into me for a few strokes. He loves his position.

Obedient Husband: Female Led Marriage: Female Led Marriage for Loving Couples
http://amzn.to/1DlQYEl
elliot had to learn. He had to learn there is only one sexuality at our house, mine. He had to learn that a bath brush leaves bruises and a cane leaves stripes. He had to learn to wear his girdle without complaining and if I tell him to wear a bra to wear one. He had to learn to be obedient. He has. At our house one of us wears the pants and the other is humbled in his panties. All that plus corner time, delicious nipple clips and a lot of well-deserved sexual frustration.

A Ladies Guide to Prostate Milking
http://amzn.to/1M5Jubu

Keeping your husband chaste is excellent discipline for him and, of course, delightful for the clever wife because your darling husband will be eager to please you. But you can add to his humiliation by relieving his spermy build up without letting him experience any orgasm at all. How? Prostate milking. Nothing easier, put your husband in some frilly panties, push a vibe in his back door and tell him to call when he wets himself. Perfect humiliation. Most ladies don’t know how to do this so here is my guide.

Corner Time
http://amzn.to/1KKJ9uu

Men, in general, are children and children need time outs for punishment. Men also need to spend a little while every day thinking about how lucky they are to have a wife like you. So, tell him to take off his clothes, all his clothes, leave his chastity cage on and send him to his corner with a pair of your well scented panties to press into the corner with his nose. Do this regularly and you’ll have a man completely, helplessly, fixated and in love with you. Many young wives don’t realize how much their husbands need and crave a firm hand…until you are ready with the whip, corner time is a good start.

You can find lots of other deliciously smutty books at our author page at:

http://amzn.to/1SU5PaM